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  • General Chemistry  (17,468)
  • Cosmology
  • Magnetism
  • thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
  • Wiley-Blackwell  (17,471)
  • Casa de Velázquez  (30)
  • 2020-2024  (30)
  • 2015-2019
  • 1995-1999  (6,853)
  • 1985-1989  (5,085)
  • 1960-1964  (4,739)
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Collection
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Year
  • 1
    Publication Date: 2024-03-25
    Description: Cuando la oralidad era imperante, siete soldados de la Monarquía sintieron la necesidad de escribir sus autobiografías en la primera mitad del siglo xvii. Entre ellos, el capitán Alonso de Contreras, cuya obra, vital, cautivó a Ortega y Gasset. Con sus plumas retrataron al Imperio, del Mediterráneo al Índico. Esa fotografía del Leviatán —el Estado Moderno—, en sus años formativos, constituye el principal propósito de este libro, en un acercamiento pragmático, inmerso en la cotidianidad, jocosa o trágica. Se siguen vidas a «salto de mata», rescatando sus sueños y tropelías, restituyendo sus vivencias y, con ellas, las de una época, así como parte de la maquinaria imperial, cuando el sol se ponía sobre la Monarquía. Todo se ensarta, en definitiva, alrededor de dos preguntas. ¿Cómo se pasó de la espada a la pluma, otro ejercicio de esgrima? ¿Cómo las dos dibujan universos, de Italia a Filipinas, pasando por España, hacia 1600-1650?
    Keywords: D1-2009 ; Z1001-8999 ; historia global ; autobiografía ; espacio imperial ; honor ; historia y literatura ; soldado ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 2
    Publication Date: 2024-03-25
    Description: Cilices, haires, disciplines sont les instruments oubliés d’une macération de la chair omniprésente dans le catholicisme tridentin, mais devenue complètement anachronique aujourd’hui. Chez les carmélites déchaussées de Thérèse d’Ávila qui sont au coeur de cet ouvrage, comme dans d’autres ordres religieux qui se caractérisent par leur austérité, on se flagelle avec vigueur et en déployant des trésors d’ingéniosité pour accroître ses peines, on ingère des immondices pour signifier sa déchéance, on fait couler le sang en abondance pour se réclamer de l’imitatio Christi, ou pour édifier ou impressionner les autres. Loin de vouloir mettre en avant les pires images de la légende noire espagnole, ce livre s’attache à dégager les logiques spirituelles, culturelles et sociales de ce dolorisme assumé mais complexe et contradictoire.
    Keywords: D1-2009 ; église catholique ; coutumes ; punitions corporelles ; carmélites ; christianisme ; religion ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 3
    Publication Date: 2024-03-25
    Description: Esta obra aborda los procesos de cambio institucional en España e Hispanoamérica durante los años que fueron desde la guerra de los Siete Años hasta la formación de los estados nacionales. Para mantener el hilo de esta historia global, dichos procesos se analizan a través del prisma de la historia de las finanzas, examinando los problemas fiscales en su interdependencia con transformaciones económicas, sociales y culturales más amplias. Resultado de dos proyectos del programa ECOS que reunieron a especialistas argentinos, franceses y mexicanos, así como a colegas de Alemania, España e Italia invitados a distintos encuentros, el libro ha intentado situarse en diferentes escalas de observación: la de la Monarquía, que negocia y reforma los mecanismos de acceso y de circulación de recursos, transformando así sus propios equilibrios políticos; o, en el otro extremo, la de las arenas locales, donde la cooperación y el conflicto de sus actores producían reconfiguraciones institucionales y territoriales; o aun el ámbito de los dispositivos que atravesaban las diferentes escalas —los derechos de propiedad, los cuerpos y las articulaciones comunitarias, o las dimensiones fiscales de la ciudadanía— cuyas evoluciones acompasaban el tránsito del Antiguo Régimen al orden republicano.
    Keywords: D1-2009 ; fiscalidad ; reformas ; instituciones ; mundo hispánico ; independencias ; América colonial ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 4
    Publication Date: 2024-03-25
    Description: Durant l'Antiquité tardive, l'épistolaire connaît un renouveau, en particulier sous l'influence du christianisme. Ce genre littéraire, hérité de la période classique, se diversifie en une correspondance très variée, qui va de la missive personnelle à la lettre pontificale. En bénéficiant de l'essor actuel des études épistolographiques, ce volume veut appréhender la lettre comme un fait culturel durant la fin de l'Antiquité et le premier Moyen Âge, avant que les règles de la rhétorique classique ne soient systématisées à partir de 1100. Sans jamais dissocier l'analyse du contenant de celle du contenu, il cherche à mieux comprendre les stratégies littéraires de ce genre protéiforme, qui oscillent entre efficacité et esthétique, et qui font de la lettre un formidable espace de liberté.
    Keywords: D1-2009 ; PN1-6790 ; Occidente cristiano ; diplomática ; género epistolar ; Edad Media ; correspondencia ; epistolografía ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 5
    Publication Date: 2024-03-25
    Description: La ausencia de una obra dedicada al estudio de los lugares de memoria de la identidad nacional española durante el franquismo constituía una laguna importante de la historiografía española que este volumen intenta completar. Se pretende aquí, por un lado, abordar el estudio del nacionalismo español durante el franquismo a la luz de la dimensión cultural y simbólica de la política, contribuyendo así a un mejor conocimiento de la evolución del discurso y de las prácticas nacionalistas a lo largo de las diferentes etapas por las que pasó el régimen, más allá de las aproximaciones puntuales o excesivamente generales. Por otro lado, y en consecuencia, se propone en este libro una perspectiva interpretativa de la nacionalización franquista que otorgue un mayor protagonismo a las prácticas culturales, simbólicas y visuales, contemplándolas en su interacción con otras identidades colectivas.
    Keywords: D1-2009 ; nacionalismo ; siglo XX ; España ; franquismo ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 6
    Publication Date: 2024-03-25
    Description: Cet ouvrage analyse le rôle médiateur de l’Espagne dans et pour l’Europe occidentale, à partir du royaume wisigoth de Tolède. Autrement dit, depuis la civilisation originale de l’Espagne entre 589, année du IVe Concile de Tolède qui voit la conversion de tout le peuple wisigoth au catholicisme, jusqu’à la chute brutale du royaume sous les coups de l’invasion islamique. Paradoxalement, cet écroulement aura servi le rayonnement européen des hommes d’Espagne, de leur idéologie, de leurs institutions, de leurs manuscrits et donc de leurs œuvres littéraires, à travers tout l’espace culturel européen, dans une dispersion féconde de l’héritage de cette Espagne wisigothique dont l’influence n’a cessé de s’exercer sur la genèse de la culture médiévale et moderne à travers l’Europe.
    Keywords: D1-2009 ; institutions ; catholicisme ; wisigoths ; idéologie ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 7
    Publication Date: 2024-03-25
    Description: Depuis une trentaine d'années, l'étude des ordres militaires au Moyen Âge a enregistré un profond renouvellement auquel Alain Demurger a particulièrement œuvré. Derrière l'histoire politique, par-delà les rouages institutionnels, la recherche s'est toujours plus attachée à considérer les hommes. Pourtant, la question des élites, s'agissant des frères, n'a jamais été analysée sinon de façon ponctuelle. En considérant à la fois les élites sociales, nobles ou citadines, les élites de pouvoir et de gouvernement et les propres élites des ordres militaires, ce livre n'apporte pas seulement un nouvel éclairage sur l'histoire des frères. Il contribue plus largement à la connaissance des sociétés médiévales, du xiie au xve siècle, depuis la péninsule Ibérique jusqu'à la Baltique et à l'Orient méditerranéen.
    Keywords: D1-2009 ; élites ; ordre militaire religieux ; Europe ; Moyen-âge ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 8
    Publication Date: 2024-03-25
    Description: En el siglo XVI, la Península Ibérica no quedó al margen del gran debate teológico que sacudía Europa. En España y Portugal se leían, comentaban y discutían los escritos de la Reforma. Su recepción no fue una mera aceptación pasiva de ideas extranjeras, sino el fruto de una interacción con planteamientos espirituales autóctonos que no puede ser reducida a la polarización entre católicos y protestantes. Las redes de creyentes evolucionaron al mismo tiempo que las doctrinas reformadas y que las estrategias de contención desarrolladas por los reyes y la Inquisición. Las contribuciones de este libro permiten un nuevo balance de la situación de la Reforma en el conjunto de la Península Ibérica, a la vez que ponen en relación a los círculos de exiliados con las comunidades del interior.
    Keywords: D1-2009 ; BL1-50 ; luteranismo ; Inquisición ; Reforma ; recepción ; herejía ; protestantismo ; censura ; siglo XVI ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 9
    Publication Date: 2024-03-25
    Description: Longtemps considéré comme une région périphérique en Méditerranée et dans l’Islam, le Maghreb médiéval est au contraire très tôt intégré dans des réseaux d’échanges, d’abord dans le cadre de la construction d’un espace islamique largement ouvert sur la mer, ensuite dans celui d’une Méditerranée dominée par les puissances latines européennes. Connecté à la fois à l’Orient, à l’Afrique subsaharienne et à la Méditerranée, le Maghreb islamique s’insère entre le viie et le xve siècle dans des connexions complexes qui donnent à ses ports un rôle croissant dans les échanges commerciaux, mais aussi plus largement dans la structuration de l’espace maghrébin et méditerranéen, à la fois comme pôles d’impulsion régionaux et interfaces entre des réseaux terrestres et maritimes. L’analyse des sources arabes et latines permet ainsi de montrer comment les acteurs politiques et économiques contribuent à faire évoluer ces réseaux commerciaux à différentes échelles, en premier lieu dans un espace centré sur les pays d’Islam, puis à partir du xie siècle dans une économie-monde en formation, connectant l’Afrique, l’Europe latine et l’Asie.
    Keywords: D1-2009 ; musulmán ; Islam ; comercio ; Maghreb ; Edad Media ; Mediterráneo ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 10
    Publication Date: 2024-03-25
    Description: Durante mucho tiempo se han considerado como un hito esencial en la historia del imperio hispanoamericano la muerte del último Habsburgo a finales del siglo xviii y la llegada al trono de los Borbones a inicios de la centuria siguiente. Como ya, en no pocos aspectos, la realidad de las provincias americanas se estaba autonomizando de los procesos de la Península, ese cambio sucedió para ellas en un contexto de dinámicas propias y de evoluciones a veces notables aunque en general mal conocidas, con las que tuvo que contar el gobierno español cuando inició las primeras reformas que prefiguraban las de la segunda mitad del siglo. Los estudios aquí reunidos tratan de esas temáticas en una perspectiva comparativa en la que resaltan las semejanzas y los procesos de diferenciación de los dos virreinatos.
    Keywords: D1-2009 ; cultura y poder ; élite ; religión ; mundo indígena ; organización territorial ; Consejo de Indias ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 11
    Publication Date: 2024-03-25
    Description: L'architecture est matériau avant que d'être forme. L'histoire traditionnelle de l'architecture tend à faire oublier cette évidence au bénéfice d'une approche dominée par des concepts stylistiques. Or ceux-ci s'avèrent toujours impropres à rendre compte de l'extraordinaire complexité du mouvement créatif qui conduit le génie humain à passer du produit manufacturé de base - ici la brique - à l'œuvre d'art qui constitue l'église, la porte de ville, le château ou la maison médiévale. L'enjeu de cet ouvrage est de montrer comment la brique s'est imposée en Espagne comme matériau de construction à la fin de l'époque médiévale, au terme d'un parcours historique au cours duquel elle fut, tour à tour et de manière infiniment variée, appréciée pour ses qualités pratiques, architectoniques, décoratives, mais aussi, de façon plus ambiguë ou subtile, pour sa légèreté, son coût modéré, sa valeur plastique, esthétique, voire idéologique. Une appréciation nuancée des caractéristiques et des modalités d'emploi du matériau, basée sur un vaste corpus d'œuvres architecturales, est seule en mesure de faire comprendre les raisons de son succès et de remettre en question un certain nombre de poncifs qui nuisent à la juste appréciation du rôle majeur joué par la brique dans l'histoire de l'architecture espagnole.
    Keywords: D1-2009 ; architecture médiévale ; construction ; Moyen-âge ; Espagne ; matériaux ; briques ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 12
    Publication Date: 2024-03-25
    Description: El presente libro versa sobre el papel de la Iglesia católica y sus misiones en los Imperios ibéricos del siglo xix y el primer tercio del siglo xx. En concreto, aborda las relaciones entre el poder civil y el eclesiástico en contextos coloniales en un período de intensa modernización de las estructuras imperiales. Con una perspectiva comparada entre los distintos espacios que componían los diferentes imperios, la obra refleja el papel que desempeñan los misioneros como un cuerpo intermedio entre colonizadores y colonizados, siempre en contacto e interacción con las poblaciones locales, así como la compleja relación entre el poder colonial y las misiones religiosas. El indudable apoyo mutuo partía de intereses que eran en parte divergentes, lo cual provocó conflictos en no pocas ocasiones. Todo ello en el marco de una relación Iglesia-Estado que, en las mismas metrópolis, no careció de importantes roces y dificultades.
    Keywords: D1-2009 ; BL1-50 ; JA1-92 ; órdenes religiosas ; Cuba ; Mozambique ; Imperios ibéricos ; Filipinas ; Guinea Ecuatorial ; sociedad colonial ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 13
    Publication Date: 2024-03-25
    Description: L'histoire des villes et des cités de l'Occident romain ne doit plus être écrite comme celle d'un déclin progressif entre le Haut-Empire et l'Antiquité tardive. Néanmoins, l'image laissée par ces communautés civiques et la cellule administrative fondamentale de l'Empire se trouble progressivement entre les iie et ive siècles. La documentation tardive, peu abondante, souvent de nature juridique ou ecclésiastique et de portée générale, rend compte de la permanence globale de la vie municipale, mais la disparition progressive des donnés épigraphiques ne permet plus de cerner sa diversité et sa richesse. Or, les vestiges archéologiques livrent un tableau contrasté de l'évolution des espaces civiques. Si leur occupation semble se pérenniser sans changement significatif dans quelques grandes villes, ailleurs la dégradation de monuments et de lieux publics ou leur occupation par des activités privées, voire leur abandon pur et simple, signalent des processus de changement dans l'activité civique qui tranchent avec la perception actuelle de la pérennité de la vie des cités. Comment faut-il interpréter cette évolution ? Faut-il y voir le témoignage d'une crise urbaine ou seulement la transformation de la pratique civique et un changement dans l'utilisation des espaces dédiés à la vie de la communauté ? S'agit-il de phénomènes diffus ou localisés ? Afin de fournir des éléments de réponse à ces questions, ce livre fondé sur un bilan mais également sur des découvertes récentes croise les Histoires provinciales, les trajectoires singulières et les destins trasversaux des villes et de l'urbanisme civique en Occident entre le Haut-Empire et l'Antiquité tardive.
    Keywords: D1-2009 ; péninsule ibérique ; urbanisme ; ville antique ; Rome ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 14
    Publication Date: 2024-03-25
    Description: Este libro explora distintos tipos de paisajes de guerra, surgidos como resultado de los grandes conflictos bélicos de la Europa del siglo pasado. Comparando el devenir de estos paisajes en Francia, España, Alemania, Rusia, Hungría, Polonia, los países bálticos, Ucrania, Camboya y Japón, se busca profundizar en sus huellas, en las reconstrucciones de la posguerra y en la patrimonialización más reciente de estos testimonios. La obra insiste en el carácter transnacional de esta historia particular de las reconstrucciones tras las contiendas, sin olvidar su dimensión artística y cultural, ni la repercusión del fenómeno en el cine y en la literatura. El volumen reúne los estudios de una veintena de especialistas que han abordado cada caso con enfoques amplios y exhaustivos donde se priorizan los elementos comparativos entre los diferentes escenarios bélicos, lo que supone una relevante aportación respecto a estos temas, que ve la luz en una edición coordinada en castellano.
    Keywords: D1-2009 ; NA1-9428 ; war ; reconstruction ; heritage ; landscape ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 15
    Publication Date: 2024-03-25
    Description: La pureté en question examine les fondements historiques et scripturaires de l’idéal de pureté partagé par les juifs et les chrétiens à la fin du Moyen Âge en péninsule Ibérique. Le croisement des sources théoriques et des documents de la pratique, des sources latines, hébraïques et vernaculaires met en évidence la façon dont ce thème majeur de la littérature biblique et talmudique s’est perpétué à travers les siècles et a eu des incidences nombreuses sur la vie quotidienne des hommes au xve s. La réflexion débouche sur des questions centrales pour l’histoire de la minorité juive en péninsule Ibérique : le passage de l’antijudaïsme à l’antisémitisme, l’apparition du concept de race, la prépondérance du sang dans l’assignation à une identité, le poids de l’accusation de crime rituel, l’incrimination des non chrétiens dans une société Ibérique de plus en plus exclusive, la discrimination et la ségrégation pour s’en protéger jusqu’à l’expulsion.
    Keywords: D1-2009 ; práctica religiosa ; pureza ritual ; antisemitismo ; judaísmo ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 16
    Publication Date: 2024-03-25
    Description: La mort de Charles II d'Espagne en 1700 et la guerre de Succession d'Espagne qui s'ensuit bouleversent toute l'Europe dont la carte en ressort transformée en 1714. Les monarchies de France et d'Espagne, longtemps rivales et concurrentes, sont devenues des alliées grâce à des souverains issus d'une même maison royale. L'ensemble de leurs relations est durablement modifié par cette alliance étroite que l'on ne tarde pas à dénommer « l'union des couronnes », nouveau cadre politique qu'il faut concevoir, mettre en pratique et défendre. Amelot de Gournay, ambassadeur de Louis XIV à Madrid, incarna la forme la plus aboutie de ces nouvelles relations. Cette étude retrace les objectifs, les succès et les échecs d'une politique à partir de sa mise en oeuvre durant un conflit qui fut aussi une guerre civile, motivé également par des impératifs commerciaux et coloniaux.
    Keywords: D1-2009 ; JA1-92 ; Grimaldo ; gobierno ; Duque de Anjou ; Guerra de Sucesión Española ; comercio ; Felipe V ; negociación ; Luis XIV ; Amelot de Gournay ; Torcy ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 17
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    Casa de Velázquez
    Publication Date: 2024-03-25
    Description: Qu’est-ce qu’une frontière romaine, comment se construit-elle ? Quelles limites le pouvoir romain conçoit-il à l’étendue territoriale de sa puissance et de ses provinces ? Telles sont les questions que pose cet ouvrage à travers l’étude de l’une des frontières les plus étendues, et encore mal connue, de l’Empire romain. Il s’agit de la frontière d’Afrique proconsulaire, qui constitue la plus longue des limites provinciales au sud de la Méditerranée. Ce livre étudie sa phase déterminante, et encore discutée, de genèse entre la fin de la République romaine et l’étape ultime d’expansion de l’occupation militaire dans le Sud de l’Africa sous les Sévères. Cette synthèse montre, à la suite d’autres études régionales, que la frontière romaine revêtait des implications politiques et territoriales à l’échelle de la province et qu’elle ne fut pas conçue en fonction d’une politique stratégique à l’échelle de l’Empire, qui ne faisait d’ailleurs pas partie des desseins de Rome pour établir localement ses frontières. Ce livre invite également à réviser l’idée encore souvent véhiculée que la frontière romaine s’est construite en Afrique par rapport, voire contre une présence nomade régulièrement surestimée, conduisant à faire de la frontière une ligne tracée ou un espace défini par la présence militaire, dans un objectif de contrôle, entre le territoire romain et les tribus voisines réputées hostiles. La notion de frontière dans le contexte de l’Afrique romaine fut effectivement fortement influencée par la fonction militaire attribuée à un grand nombre de vestiges découverts dans le sud du territoire provincial. Les motifs justifiant la présence de l’armée romaine dans la région demeurent toutefois débattus. La question tout à fait centrale qui se pose est alors celle du nomadisme, puisque c’est autour de l’existence présumée de pratiques nomades ou semi-nomades que sont traditionnellement perçues les relations entre Rome et les populations locales africaines dans le Sud de l’Afrique romaine. Cette étude montre que la limite provinciale, dotée progressivement de structures militaires, ne constitua pas sous le Haut-Empire une frontière militaire institutionnalisée et prenant la forme de districts militaires ou administratifs établis. Telle n’était pas l’ambition de Rome, dont l’intervention dans le Sud de l’Africa ne répondait pas à un souci de pacification intégrale du territoire. Ce constat, qui n’est pas spécifique au contexte africain, explique aussi le pragmatisme dont Rome fit preuve dans les choix présidant à l’implantation des garnisons à la frontière provinciale, qui ne participaient pas elles-mêmes à une politique réfléchie d’occupation militaire systématique de la zone. L’examen de l’ensemble de la documentation, écrite et archéologique, conduit aussi à réviser l’idée d’un contrôle effectif et régulier qui aurait été opéré à la frontière de l’Afrique proconsulaire. Il permet en outre d’aborder sous un angle original la nature du peuplement dans la région, et de prendre la mesure de ce que représentait au quotidien la frontière provinciale pour les populations qui étaient établies à son contact. Ces différents aspects sont envisagés à travers trois parties successives, qui constituent l’armature de l’ouvrage. La réflexion est initiée par l’étude des circonstances ayant concouru à la formation de la frontière africaine, entre la fin de la République et le début du Principat. L’enquête vise à comprendre la nature des relations entre l’État romain et les populations locales dans le processus d’appropriation du territoire africain, progressivement soumis à Rome. Ce préalable indispensable permet d’envisager dans un deuxième temps les mesures politiques et les structures militaires organisant peu à peu la frontière provinciale sous le Haut-Empire. À travers l’examen critique des différentes manifestations de l’autorité romaine, à la fois en termes de décisions, mais aussi de constructions, l’enjeu est de mieux comprendre la gestion, par Rome, des confins de son Empire. Les dynamiques territoriales, auxquelles la dimension spatiale reconnue aux frontières africaines octroie une place essentielle, sont enfin étudiées dans une troisième partie. Celle-ci envisage les incidences de la frontière pour les populations établies à son contact, à la fois en termes d’échanges économiques et d’évolutions internes à l’organisation de ces sociétés. Le résultat des données observées invite alors à réfléchir sur l’émergence d’un territoire de la frontière, au sud de la province africaine, dès la période du Haut-Empire.
    Keywords: D1-2009 ; desierto ; África romana ; Alto Imperio ; Legio III Augusta ; frontera ; Garamantes ; Nasamones ; armada ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 18
    Publication Date: 2024-03-25
    Description: Ce volume porte sur les productions culturelles liées aux révoltes et révolutions survenues dans les possessions des Habsbourg d’Espagne aux xvie et xviie siècle, tant dans la péninsule Ibérique qu’en Italie, dans les Flandres ou dans le Nouveau monde. Il s’agit d’étudier différentes formes d’expression (écrites, iconographiques, architecturales, cérémonielles) employées par les révoltés ou par les autorités afin de légitimer ou de diffuser leur action.
    Keywords: D1-2009 ; revueltas ; propaganda ; modelos politicos ; panfletos ; Monarquía Hispánica ; levantamientos ; Casa de Austria ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 19
    Publication Date: 2024-03-25
    Description: Les populations de la Méditerranée occidentale (Espagne, France méridionale, Italie) témoignent dans les derniers siècles du Moyen Âge d’une ouverture croissante aux échanges, dont rendent compte la densification rapide du réseau des marchés locaux, le recours massif au crédit et l’intensification de la circulation des biens. Cet ouvrage aborde cette « commercialisation » de la société médiévale du point de vue du consommateur plutôt que de celui du marchand, plus traditionnel dans l’historiographie. Par l’analyse des cultures de consommation des clientèles, de leurs stratégies d’acquisition des produits et du dispositif de régulation protégeant les approvisionnements domestiques, il s’agit de mieux comprendre ce que « faire son marché » signifia pour les hommes et les femmes de ce temps.
    Keywords: D1-2009 ; intercambio ; mercado ; Edad Media ; consumidor ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 20
    Publication Date: 2024-03-25
    Description: La lettre diplomatique tire son argument d'une réalité très généralement reconnue des diplomatistes : ils manipulent des textes qui empruntent au genre épistolaire. Durant le haut Moyen Âge, de nombreux actes étaient rédigés sous forme d'épître, en conservant de la rigueur formelle du genre l'adresse et le salut. Ce ne fut qu'à partir de l'époque carolingienne que l'acte diplomatique prit ses distances pour acquérir des caractéristiques formelles qui l'éloignèrent de la forme épistolaire. Celle-ci ne disparut toutefois pas. Elle redevint même prépondérante à partir du xiiie siècle et du renouveau de l'ars dictaminis dans l'Occident chrétien. Le présent ouvrage explore ce jeu d'attraction entre les genres, le va-et-vient formel et fonctionnel de l'acte à la lettre, et les enjeux d'écriture, de pouvoir et de mémoire découlant de cette hybridation.
    Keywords: D1-2009 ; PN1-6790 ; carta ; Occidente cristiano ; epistolaridad ; práctica escrituraria ; diplomática ; Edad Media ; correspondencia ; epistolografía ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 21
    Publication Date: 2024-03-25
    Description: Minas de Riotinto, 4 février 1888 : des milliers de mineurs et d’habitants des villages alentour manifestent contre les calcinations de pyrites à l’air libre pratiquées par la Rio Tinto Company, dont les fumées toxiques affectent gravement la santé publique, l’agriculture, l’environnement. Placée au milieu d’une foule pacifique, l’armée tire sans sommation, faisant près de 200 morts, bilan travesti par les autorités, sans équivalent dans l’Europe du temps. À partir de centaines de documents d’archives inédits, cet ouvrage inscrit le drame de « el año de los tiros » dans une décennie de luttes locales tout en décryptant les stratégies et responsabilités des différents pouvoirs, compagnie minière, politiques, experts. Le conflit et le massacre conduisent à une réflexion sur le fonctionnement même du régime de la Restauration et, au-delà de l’Espagne, sur les comportements des populations et de l’ensemble des acteurs devant une catastrophe environnementale.
    Keywords: D1-2009 ; catastrophes environnementales ; industrie minière ; impérialisme ; Rio Tinto Company ; Restauration ; Andalousie ; protestation populaire ; XIXe siècle ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 22
    Publication Date: 2024-03-25
    Description: Dominant les espaces occidentaux, les Pyrénées n'ont jamais été perçues autrement que comme une frontière. Rome en fit une limite : limite de son expansion en Ibérie, puis limite administrative entre les provinces gauloises et hispaniques. Si chaque versant évoluait désormais séparément, comme se tournant le dos, à l'intérieur des cadres juridique, économique et culturel mis en place avec la domination romaine, celle-ci fut loin de gommer entièrement la spécificité même des Pyrénées : celle d'un pays de frontière, milieu profondément original, vivant non plus selon ses propres lois mais conservant ses modes de vie, coutumes et traditions que la romanisation respecta, voire renforça.
    Keywords: D1-2009 ; frontière ; Pyrénées ; voie romaine ; Espagne ; France ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 23
    Publication Date: 2024-03-25
    Description: Nec plus ultra : « et pas au-delà ». Cette locution nourrie des mythes antiques entourant le détroit de Gibraltar est une création de Charles Quint, le conquérant du Nouveau Monde. Sa devise Plus oultre marquait son désir de dépasser la puissance romaine. Mais Rome a-t-elle toujours envisagé l’Extrême Occident méditerranéen comme un nec plus ultra, comme les confins immuables et indépassables de son empire ? Les espaces des colonnes d’Hercule, polarisés par Cadix et Tanger, ont moins représenté des bornes infranchissables pour les Romains que les montants d’un seuil, à la fois une protection de la mer Intérieure et une ouverture sur l’Océan. Cet Extrême Occident, ces Portes du Soir du mythe héracléen, ont donc été un enjeu crucial dans l’élaboration de l’Empire romain, des guerres puniques jusqu’à la Tétrarchie.
    Keywords: D1-2009 ; Gibraltar ; Extremo Occidente ; integración política ; imperio romano ; Mauritania Tingitana ; Mediterráneo ; Hispania ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 24
    Publication Date: 2024-03-25
    Description: La transition vers la démocratie occupe une place de choix dans l'imaginaire espagnol. Miroir positif de la tragédie représentée par la Guerre civile de 1936-1939, vantée à l'extérieur comme un modèle à suivre, cette transition est devenue en Espagne un mythe fondateur. Réputée pacifique, elle n'aurait pas, ou peu, fait couler le sang. Ce livre souligne pourtant le contraire. À partir de données inédites, il conclut à l'existence d'un cycle de violences qui, loin d'être à mettre sur le seul compte de l'ETA, est imputable à des protestataires de tous bords ainsi qu'aux agents de l'État parfois enclins à la bavure. Cet ouvrage se penche sur les motivations et les pratiques des acteurs ainsi que sur la réforme du système répressif franquiste, entachée par le recours à la torture ou à la « guerre sale » contre un terrorisme croissant. Il décrypte en outre le poids des imaginaires dans une Espagne traumatisée par un passé douloureux que réactive la violence du présent. Ainsi, en replaçant la violence et sa mémoire au cœur de l'analyse, il contribue à renouveler l'interprétation de cette période clef de l'Espagne contemporaine. S. B.
    Keywords: D1-2009 ; violence politique ; démocratie ; politique ; Espagne ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 25
    Publication Date: 2024-03-25
    Description: En la segunda mitad del siglo xv se abrió un ciclo particularmente brillante para la cultura escrita cuyas consecuencias pueden rastrearse durante toda la Edad Moderna y, aún más, en los siglos contemporáneos. A fin de analizar algunas de sus manifestaciones, este libro se interesa especialmente por las formas gráficas y significados de las escrituras expuestas, desde la inscripción renacentista a la pintada política en la dictadura chilena; las prácticas epistolares en cuanto que testimonio de la importancia social de la comunicación escrita; los libros de memorias, considerados como objetos donde se configura la memoria personal y familiar, susceptibles incluso de ser interpretados en clave autobiográfica; y por último, distintos acercamientos a la apropiación de los textos con la mirada puesta en los consumidores e intermediarios, desde la nobleza culta hasta los lectores más «débiles», prestando atención tanto a la cultura manuscrita como a la impresa entre los siglos xvi y xix. Frente al fetichismo libresco que caracteriza no pocas aproximaciones a la Historia de la Cultura Escrita, esta obra se interesa por esta en la diversidad de sus formas textuales –epigráficas, murales, manuscritas o impresas, permanentes y efímeras–, pues solo así se puede captar la riqueza de cuanto una determinada sociedad, integrada por gentes de letras pero también por semialfabetizados y analfabetos, escribe y lee. Culturas del escrito, en suma, que certifican la vitalidad de esta corriente de investigación y tratan de contribuir a la Historia que escribimos en estos tiempos de incertidumbre.
    Keywords: D1-2009 ; historia ; comunicación ; escritura ; Occidente ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 26
    Publication Date: 2024-03-25
    Description: Avant le temps des ministres-favoris de l’époque baroque, les rois de l’Europe médiévale ont compté dans leur proximité sur l’assistance de personnages souvent vus comme leur préfiguration. Cette expérience de la privauté n’est cependant pas partout de même intensité. Ainsi, la Castille de la fin du Moyen Âge se distingue-t-elle par une continuité d’expérience. Ce terrain s’avère donc particulièrement propice pour interroger l’identité de la privauté médiévale, son sens historique. La privauté (privanza) est un choix, celui de l’amitié contre la parenté. Réalisé sur le terrain idéologique à partir du milieu du xiiie siècle, ce choix se fait stratégique au début du xive siècle : contre ses parents et ses barons, qui entendent exercer une emprise sur sa royauté, le roi lance ses créatures, les privados, pour s’en libérer. Si ceux-ci oeuvrent donc à une expulsion, ils organisent dans le même temps une participation alternative et plus large au gouvernement du roi, celui de sa personne et de son royaume. La privauté fait ainsi sentir quel dépassement sociétal affecte la compagnie royale à partir du xiiie siècle. Et la répétition des expériences de privauté au xive siècle fonde un régime politique, marqué par la distinction entre gouvernement et souveraineté. Cet essai envisage à nouveaux frais ce moment fondateur de l’expérience médiévale du pouvoir d’État.
    Keywords: D1-2009 ; privanza ; amistad gubernamental ; soberanía ; régimen político ; Edad Media ; Castilla ; privado ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 27
    Publication Date: 2024-03-25
    Description: Le problème du salut personnel et collectif, crucial pour tous les chrétiens, entraîne l’émergence d’individus et de groupes sociaux réputés particulièrement aptes à faire leur propre salut et à œuvrer pour celui des autres. Partant de cette donnée fondamentale, le présent ouvrage examine la tension entre les ambitions spirituelles et les contraintes individuelles, communautaires et institutionnelles des moines, des chanoines réguliers et des frères mendiants, dans le cadre du Moyen Âge hispanique. Trois modalités d’accès au salut sont mises en évidence : la conversion, c’est-à-dire le choix d’entrer en religion et la continuelle transformation individuelle qu’il suppose ; la médiation, fondée sur la prière et sur la liturgie ; le soin des âmes enfin, lié à l’engagement pastoral.
    Keywords: D1-2009 ; BL1-50 ; religión ; cristianismo ; religioso ; España ; laico ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 28
    Publication Date: 2024-03-25
    Description: Comment les acteurs économiques se déterminent-ils face aux choix cruciaux qu’ils sont amenés à faire au cours de leur existence ? Sont-ils guidés par le seul « goût du lucre » ? Ou par des calculs plus complexes, prenant en compte leur environnement social, familial et culturel ? Cette question ancienne, mais toujours d’actualité, aussi bien au sein des sciences sociales que dans le débat public, est abordée ici à partir de l’observatoire singulier des quelque 500 marchands français qui s’étaient installés à Cadix au xviiie siècle pour bénéficier des conditions commerciales exceptionnelles qu’offrait alors le grand port andalou de la Carrera de Indias - la mythique route du commerce colonial espagnol et des « fabuleux métaux ». À travers l’histoire de leurs trajectoires dans les temps troublés des guerres révolutionnaires, de l’épopée napoléonienne et de l’émancipation des colonies espagnoles, c’est à une plongée au cœur des logiques de décision des acteurs que nous invite l’auteur.
    Keywords: D1-2009 ; negocios marítimos ; historia económica ; comercio colonial ; Cadiz ; mercaderes extranjeros ; Carrera de Indias ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 29
    Publication Date: 2024-03-25
    Description: Los trabajos de este libro permitirán al lector hacerse con una visión comparada de la relación que la inmigración, el funcionamiento de los mercados de trabajo y el servicio doméstico han establecido entre sí en el seno de diferentes ciudades europeas en el curso de los siglos XVIII, XIX y XX. La novedad de los mismos no solo se aprecia en los resultados que ofrecen, sino también en los métodos que buena parte de ellos emplean. El recurso a la información de las bases nominativas permite estudiar desde un punto de vista original cuestiones tales como las redes de paisanaje, los efectos de la movilidad social y laboral del servicio doméstico, la diferente plasmación de los proyectos migratorios de las mujeres o la relevancia que en ciertos casos tuvo la población flotante.
    Keywords: D1-2009 ; H1-99 ; inmigración urbana ; servicio doméstico ; mercados de trabajo ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: Spanish
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  • 30
    Publication Date: 2024-03-25
    Description: En 1713, après deux siècles de domination en Italie et aux Pays-Bas, le traité d’Utrecht sanctionne le démembrement de la monarchie hispanique et son repli dans la péninsule Ibérique. Alors que l’Espagne semble désormais tourner le dos à l’Europe, des milliers de Flamands et d’Italiens empruntent pourtant le chemin de l’exil pour rester sous la sujétion du Roi Catholique. Contre toute attente, ces exilés ont été constitués en une puissante élite politique et militaire qui a pesé durablement dans le gouvernement de la monarchie. Partant du cas des Flamands, cet ouvrage interroge les circonstances de la désagrégation impériale et ses conséquences sur la société espagnole. Loin des clichés du repli péninsulaire, en décryptant à hauteur d’homme les horizons politiques de ce collectif d’exilés, il propose une lecture de la façon dont les Bourbon ont reconfiguré l’héritage impérial de l’Espagne en Europe.
    Keywords: D1-2009 ; Países Bajos Españoles ; Guardia Valona ; Guerra de Sucesión Española ; Felipe V ; Ejército ; Extranjeros ; thema EDItEUR::D Biography, Literature and Literary studies::D Biography, Literature and Literary studies::DN Biography and non-fiction prose
    Language: French
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  • 31
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 57-60 
    ISSN: 1434-193X
    Keywords: Benzyne ; Dehydroanthracene ; Matrix isolation ; Photochemistry ; Bergman reaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -9,10-Didehydroanthracene (1) is an interesting derivative of p-benzyne that has been subject of several studies. In contrast to an earlier report, the photochemical decarbonylation of 9,10-dicarbonyl-9,10-dihydroanthracene (2) does not lead to 1 but rather to the ring-opened ene-diyne 4. The key intermediate for this reaction is keto carbene 7 which is formed by monodecarbonylation of 2. Carbene 7 is labile towards visible-light irradiation and easily looses the second CO molecule to give 4. Carbene 7 and diyne 4 are characterized by IR and UV/Vis spectra, the IR spectra are compared to calculations at the B3LYP/6-31G(d,p) level of theory.
    Additional Material: 2 Ill.
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  • 32
    ISSN: 1434-193X
    Keywords: Nucleophilic addition ; Solvent effect ; Reversal of diastereoselectivity ; Temperature effect ; Imines ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Commonly observed, but rarely explored, is the possibility of modifying the diastereomeric excess (de%) by means of temperature. A complete reversal in the diastereofacial selectivity could be obtained whenever the diastereoisomers concerned are differentially favored by enthalpy and entropy. The enthalpic or entropic dominance of a diastereoisomer depends greatly on the reaction solvent used.
    Additional Material: 1 Ill.
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  • 33
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 73-81 
    ISSN: 1434-193X
    Keywords: Donor-acceptor systems ; Cage compounds ; Stelladione ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A number of condensations could be carried out using tricyclo[3.3.0.03,7]octane-2-one (stellanone, 4) and tricyclo[3.3.0.03,7]octane-2,6-dione (2,6-stelladione, 5) as starting materials. The components for condensations were 2-trimethylsilyl-1,3-dithiane (6), 1,1-bis(trimethylsilyl)-1H-cyclopropa[b]naphthalene (7), its 3,6-dimethoxy-substituted analogue 8, fluorene (12), xanthene (13), diethyl malonate (14), and malononitrile (15). The condensation reactions with 5 yielded mono- and disubstituted products, among them were the donor-acceptor-substituted 2,6-stellanes 33-35. The structures of 18 (prepared from stellanone and fluorene), 19, 24, 27, 31 and 32 (synthesized by condensation of 2,6-stelladione and 2-trimethylsilyl-1,3-dithiane and malononitrile, respectively) were determined by X-ray crystallography.
    Additional Material: 1 Ill.
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  • 34
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 87-90 
    ISSN: 1434-193X
    Keywords: Water ; α-Nitrocycloalkanones ; ω-Nitro acids ; Surfactant ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The reaction of various α-nitrocycloalkanones 1 with aqueous 0.05 M NaOH, at 80 °C, in the presence of cetyltrimethylammonium chloride (CTACl) as a cationic surfactant, produces ω-nitro acids 2 in good yields. Reduction of the latter with HCOONH4/Pd-C, in methanol, at 80 °C affords ω-amino acids 3. The synthesis of methyl 9-oxodecanoate (8) is also reported.
    Additional Material: 2 Tab.
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  • 35
    ISSN: 1434-193X
    Keywords: O-Alkylation ; Ambident nucleophile ; Thiazolethione ; Thiohydroxamic acid ; Phase-transfer reaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -O-Alkylation of cyclic thiohydroxamic acids 1 and 3-5 has been studied with a view to developing an efficient method for the synthesis of N-(alkoxy)pyridine-2(1H)-thiones and N-(alkoxy)thiazole-2(3H)-thiones. Four issues have been addressed and the following conclusions can be drawn: (i) Thiones 1 and 5 exist as O-H acids in the solid state. (ii) According to NMR investigations (1H, 13C), the thione structures should be largely retained in CDCl3, [D6]DMSO, and CD3OD solutions of acids 1, 3-5, as is also the case for pyridinethione salts 2a-h. (iii) O-Alkylation of pyridinethione salts occurs in competition with S-alkylation. Selective O-alkylation is however possible, if thiohydroxamate salts with large countercations, such as M = NBu4, are treated with hard alkylating reagents in polar aprotic media. (iv) As tetrabutylammonium thiohydroxamates, such as 2f, are highly useful in the synthesis of cyclic thiohydroxamic acid O-esters, we have developed an efficient protocol for the preparation of N-(alkoxy)pyridine-2(1H)-thiones directly from acid 1 using phase-transfer conditions (alkyl halide or sulfonic acid ester, CH3CN, K2CO3, Bu4NHSO4). This method has proved particularly successful for the synthesis of N-(alkoxy)thiazole-2(3H)-thiones 11, 20-28, which were obtained in yields of up to 87%.
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  • 36
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    Liebigs Annalen 1999 (1999), S. 129-134 
    ISSN: 1434-193X
    Keywords: Tetrahydro-2-vinylquinoxaline ; Cyclization ; Palladium ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Reaction of (Z)-1,2-bis(methoxycarbonyloxy)but-2-ene (2) with various N,N-bis(arylsulfonyl)-o-phenylenediamines 1 was catalyzed by a palladium complex associated with chiral ligands to give optically active 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydro-2-vinylquinoxalines 3 with up to 62% ee. The use of (S)-MeOBIPHEP as the chiral ligand and N,N-bis(p-tolylsulfonyl)-o-phenylenediamine (1i) as the nucleophile led to the highest ee at 25 °C, regardless of the solvent used. The enantioselectivity of the cyclization is strongly affected by the nature of the substituents at the nitrogen atom.
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  • 37
    ISSN: 1434-193X
    Keywords: Fluorine ; Lactones ; Annulation ; Ketene ; Sulfoxides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enantiomerically pure α,α-dichloro β-fluoroalkyl γ-p-tolylthio γ-butyrolactones trans-6a-c have been obtained with excellent stereocontrol (〉 98:2) and enantiomeric purity (〉 98:2) by sulfoxide-directed lactonization (Marino's annu-lation reaction) of β-fluoroalkyl vinyl sulfoxides (R)-(E)-5a-c with dichloroketene. Highly chemoselective dechlorination and desulfurization reactions performed on trans-6c efficiently provided the β-chlorodifluoromethyl γ-butyrolactone (S)-8c, the absolute stereochemistry of which was determined by X-ray diffraction analysis of its γ-p-tolylthio precursor (2R,3S)-7c.
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  • 38
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    Liebigs Annalen 1999 (1999), S. 141-143 
    ISSN: 1434-193X
    Keywords: Nitrosobenzene ; 4-Methoxy-N-methyleneaniline ; 1,3,5-Tris(4-methoxyphenyl)-1,3,5-triazinane ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A 1:1 adduct produced in the reaction of nitrosobenzene (2) with 1,3,5-tris(4-methoxyphenyl)-1,3,5-triazinane (3) has been shown by X-ray diffraction structure analysis to be the N′-(4-methoxyphenyl)-N-phenyl-N-oxyformamidinium species 5.
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  • 39
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    Liebigs Annalen 1999 (1999), S. 155-161 
    ISSN: 1434-193X
    Keywords: Alkylation ; Oxazolines ; anti-α-Alkyl α-hydroxy β-amino acids ; Lithium dianion ; Penicillin G acylase ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -As part of an ongoing project concerning the synthesis of enantiomerically pure α-hydroxy β-amino acids, we have now developed a general strategy allowing the synthesis of anti-α-alkyl α-hydroxy β-amino acids. Our procedure involves the intermediate formation of trans-oxazolines, which are alkylated at C-5 with good to high diastereoselectivity and then hydrolysed under mildly acidic conditions, affording in quantitative yield the corresponding hydroxy amides. The starting (R)-3-amino-3-phenylpropanoic acid and (S)-3-aminobutanoic acid were obtained in enantiomerically pure form by selective enzymatic hydrolysis of the corresponding phenylacetylamides with penicillin G acylase.
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  • 40
    ISSN: 1434-193X
    Keywords: Palladium catalysis ; Homogeneous catalysis ; Anilines ; Alkylation ; Oxazolidinones ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Palladium-catalyzed reaction of acidic anilines with (Z)-2-butene-1,4-diyl dicarbonate affords N-aryl-4-vinyloxazolidin-2-ones. The success of the reaction depends on the acidity of the aniline and requires in situ conversion of the dicarbonate into carbamate carbonate by nucleophilic attack of the aniline conjugate base followed by palladium-catalyzed intramolecular cyclization.
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  • 41
    ISSN: 1434-193X
    Keywords: Density functional calculations ; Vinylcyclopropane-cyclopentene rearrangement ; [1,3]-Sigmatropic shift ; Biradical-like transition structure ; Substituent effects ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The effect of donor substitution by the hydroxy group and of acceptor substitution by the cyano group on the activation energies of the vinylcyclopropane-cyclopentene rearrangement was calculated by the spin-restricted RB3LYP/6-31G* method for reactant structures and by the spin-unrestricted UB3LYP/6-31G* method for transition structures. The activation energies of the rearrangement of hydroxy- and cyano-substituted vinylcyclopropanes are very similar for substitution in the same position. In agreement with earlier findings the substituent effects on the activation energies are closely connected with the radical stabilizing properties of the substituents. As indicated by singlet/triplet splitting energies, the transition structures are essentially biradicaloid. In spite of spin pairing in the transition structure the substituent effects on bond lengths and on stabilization energies are very similar to those of the free radicals corresponding to the two radical substructures. Thus, the transition structures may be considered, in good approximation, as structures consisting of two weakly interacting radicals.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98349_s.pdf or from the author.
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  • 42
    ISSN: 1434-193X
    Keywords: Cyclopropanes ; Rearrangements ; Cyanohydrins ; Schiff bases ; Small ring systems ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The direct cyclization of 2-amino-4-chloro-3,3-dimethylbutanenitrile with potassium tert-butoxide in THF afforded 1-amino-2,2-dimethylcyclopropane-1-carbonitrile and a dimerization product. Various new cis- and trans-1-(tert-butylamino)-2-benzyl-2-methylcyclopropane-carbonitriles and© the corresponding cyclopropanecarboxamides have been synthesized, with focus on the isolation of the pure stereoisomeric cyclopropanecarboxamides. The relative configuration of the stereoisomers was established by X-ray crystallographic analysis of one of the model compounds. A new route to the latter functionalized cyclopropanes was developed by reaction of 1-methoxycyclopropylamines with potassium cyanide. Some remarkable rearrangements of 1-aminocyclopropane-1-carbonitriles into azetidine and oxazine derivatives via Favorskii-derived intermediates are reported. Various aspects of the chemistry of geminally functionalized cyclopropanes are discussed.
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  • 43
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    Liebigs Annalen 1999 (1999), S. 267-275 
    ISSN: 1434-193X
    Keywords: Vinylallenes ; Organocuprates ; Substitution ; Stereoselective synthesis ; Copper catalysis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enyne acetates 2, 4, 6, and 8, as well as enyne oxiranes 10, with different substitution patterns react with organocuprates regioselectively under 1,5-(SN2′′)-substitution to provide vinylallenes 11 and 12. With lithium dimethylcuprate, reduced vinylallenes originating from a (formal) transfer of a hydride ion to the substrate are formed in some cases. The products are usually obtained as mixtures of (E/Z)isomers; however, pure (E)-vinylallenes are formed occasionally. The 1,5-substitutions can also be carried out with catalytic amounts of copper reagents. The reaction of chiral enyne acetate (S)-2a with tBu2CuLi · LiCN proceeds enantioselectively, so that this transformation constitutes a new case of remote stereocontrol.
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  • 44
    ISSN: 1434-193X
    Keywords: Nitrogen heterocycles ; Open-chain analogue of Reissert compound ; Hydrofluoroborate salts ; α,β-Ethylenic esters ; 1,3-Dipolar cycloaddition ; Azomethine ylide ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The reaction of the hydrofluoroborate salt of an open-chain analogue of a Reissert compound with some α,β-ethylenic esters does not give a [4 + 2] cycloadduct, as previously described in the case of ethyl acrylate. The reaction starts with a 1,3-dipolar cycloaddition of a münchnone imine 5c, d. The [3 + 2] cycloadducts 13 evolve via a rearrangement-condensation sequence to give a substituted 2-pyridone derivative 18 or 19. The proposed mechanism has been verified by the isolation and structural X-ray analysis of some compounds of the reaction sequence.
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  • 45
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    Liebigs Annalen 1999 (1999), S. 335-360 
    ISSN: 1434-193X
    Keywords: 2-tert-Butylhydropyrimidinones ; 3-Aminocarboxylic acid derivatives ; Cyclic imino esters ; Lithium enaminates ; Alkylations ; β-Amino acids ; Asymmetric synthesis ; Kinetic resolution ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Racemic and enantiopure 2-tert-butyltetrahydropyrimidinones (from pivalaldehyde and 3-aminocarboxylic acids) are converted to Alloc-, Boc-, and Z-protected cyclic imino esters (7-10, Schemes 2-4). These are deprotonated to Li enaminates (K, L). Reactions with electrophiles (prim., sec. alkyl, allyl, benzyl, propargyl halides, aldehydes, imines, enoates) give good yields and are highly diastereoselective (products 11-42, Schemes 5-10). A two-step cleavage (removal of protecting group and hydrolysis) under very mild conditions converts the heterocyclic products to α-branched β-amino acid methyl esters (43-61, Schemes 11-13). The structure of the products is determined by NMR spectroscopy (Figure 1), by chemical correlation (Scheme 14), and by X-ray analysis (Figure 2, 3, 7, Table 1). A structure of the Li enaminates is proposed (Figure 4). Mechanistic models are derived for the reactions occurring with formation of two stereogenic centers with relative topicity like (Figures 5, 6).
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  • 46
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    Liebigs Annalen 1999 (1999), S. 373-378 
    ISSN: 1434-193X
    Keywords: Alkaloids ; Cross-coupling ; N-Heterocycles ; Palladium ; Synthesis design ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Thermal or acetyl chloride induced cyclization of bromoenamide 10 affords the pentacyclic derivative 12 with high yield and regioselectivity. From this common synthetic intermediate, palladium-catalyzed reactions allow the total synthesis of indolopyridine alkaloids 1-6.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98332_s.pdf or from the author.
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  • 47
    ISSN: 1434-193X
    Keywords: Reverse-turn mimics ; γ-Turns ; β-Turns ; β-Hairpins ; NMR spectroscopy ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The solid-phase synthesis and characterization of a series of peptides (3-9), containing reverse-turn mimetic bicyclic lactams (1a, 1b), was reported in the preceding paper. The bicyclic lactams (1a, 1b) possess high structural similarity to the two central residues of a β-turn. The conformational preferences of the constrained peptides have been investigated by NMR spectroscopy and IR spectroscopy. Our experimental results have been complemented by computer modelling studies and show that the constrained peptides (3-9) form an inverse γ-turn or a type-II′ β-turn through intramolecular hydrogen bonding, depending on the nature of the reverse-turn mimic. In N-acetylated tetrapeptide mimics incorporating the two different bicyclic lactams (a series and b series), H5 is available for either a γ-turn (7-membered ring with the carbonyl group of the bicyclic lactam) or a β-turn (10-membered ring with the carbonyl group of residue 2), as shown in Figures 7 and 9. The a series incorporating the (5,7)-bicyclic lactam predominantly induces the γ-turn conformation, while the b series incorporating the (5,6)-bicyclic lactam can promote either a γ-turn or a β-turn conformation, with the β-turn usually being preferred and with varying degrees of β-hairpin formation.
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  • 48
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    Liebigs Annalen 1999 (1999), S. 409-417 
    ISSN: 1434-193X
    Keywords: Deprotonation ; Oxiranyloxazolines ; Oxazolinyloxiranyllithium compounds ; Oxazolidines ; Acyloxiranes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at -100 °C in Et2O furnishes oxazolinyloxiranyllithium compounds[1]1b, 1i, and 1l which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c-1g and 1j. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-(4,4-dimethyl-2-oxazolinyl)-2-p-tolylepoxyethane (1h) was found to be configurationally stable while oxiranyllithium 1l, generated from the cis isomer 1k, was not. Oxazolinylepoxides 1d, 1j, and 1m could be deblocked to acyloxiranes 5a-e through oxazolidines 4a-e.
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  • 49
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    Liebigs Annalen 1999 (1999), S. 419-430 
    ISSN: 1434-193X
    Keywords: Electrochemistry ; Electrosynthesis ; Nitrosobenzenes ; Nitrogen heterocycles ; 1-Aminoindoles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -An electrochemical methodology offering efficient access to N-alkyl- and N-aryl-substituted 1-aminoindoles has been developed. N-Substituted 2-(ortho-nitrosophenyl)ethylamines, electrogenerated in a “redox” flow cell, undergo intramolecular cyclization to hydrocinnoline-type intermediates. Under slightly basic conditions, these undergo spontaneous ring-contraction to produce the N-substituted heterocycles in good yields. The reactions have been studied in slightly acidic and slightly basic aqueous alcoholic media.
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  • 50
    ISSN: 1434-193X
    Keywords: Aminoacylsilanes ; Amino aldehydes ; Amino alcohols ; Allylation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A practical route is described for the synthesis of enantiopure β- and γ-amino alcohols with two stereocenters, starting from homochiral α- (1 and 5) and β- (13 and 16) -aminoacylsilanes, and involving stereoselective addition of allylmetal compounds and subsequent stereospecific protiodesilylation of the adducts. The degree of diastereoselectivity achieved in the nucleophilic addition step depends on both the nitrogen-protecting group and the reagents used. Diastereomeric excess (de) values equal to or higher than 98% were obtained in the TiCl4-promoted allylation of the N-Pht-aminoacylsilanes 1 and 13 and of the N-Ts-aminoacylsilane 5 with allyltrimethylsilane. Lower de values were obtained in the Sc(OTf)3-catalyzed allylation of 5 with tetraallyltin and in the additions of both allyltrimethylsilane and tetraallyltin to the N-Ts-β-aminoacylsilane 16. Protiodesilylation of the adducts, leading to the β- and γ-amino alcohols, was accomplished with TBAF, except in the case of the adducts obtained from 5. For these, a preliminary removal of the tosyl group was necessary, which was accomplished with simultaneous desilylation by treatment with Na in liquid ammonia.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98342_s.pdf or from the author.
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  • 51
    ISSN: 1434-193X
    Keywords: meta Photocycloaddition ; Photochemistry ; Steric hindrance ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Irradiation of a series of 5-(2-methoxyphenyl)pent-1-enes substituted with a hydroxy or trimethylsilyloxy group at the α-, β-, or γ-position of the side-chain yields in all cases meta photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that the diastereoselectivity originates from minimization of steric interactions between the side-chain substituent and the ortho-methoxy group at the arene unit. Hydrogen bonding does not seem to be involved. The introduction of the side-chain substituents also influences the regioselectivity of the addition: The linear to angular adduct ratios are significantly increased compared to the case of the parent compound.
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  • 52
    ISSN: 1434-193X
    Keywords: 5-Aza-7-deaza-2′-deoxyguanosine ; Oligonucleotides ; Parallel DNA ; Protonated base pairs ; Tm values ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Oligonucleotides containing 5-aza-7-deaza-2′-deoxyguanosine (1) were synthesized. Solid-phase synthesis was performed with the phosphonate 15 or the phosphoramidite 5. The amino-unprotected phosphonate 4 was also employed. Hybridization studies of oligonucleotides containing 1 resulted in new base pairs leading to duplexes with parallel (ps) or antiparallel (aps) chain orientation. Among those with parallel chains a stable “purine-purine” base pair was observed between 5-aza-7-deazaguanine and guanine or 7-deazaguanine. Antiparallel stranded duplexes are formed when 5-aza-7-deazaguanine pairs with cytosine. This base pair has only two hydrogen bonds under neutral conditions but is stabilized by a third one in acidic medium. A new base pair is also detected between the base of 1 and isoguanine (neutral medium).
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  • 53
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    Liebigs Annalen 1999 (1999), S. 523-523 
    ISSN: 1434-193X
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -By mistake wrong concentrations were given in the footnote of Table 1 and in the Discussion. Instead of c0 = 1.2 M read c0 = 0.12 M if 2-naphthalenethiol was used as hydrogen donor and instead of c0 = 1.8 M read c0 = 0.18 M if Bu3SnH was used to trap photoproducts. In Table 2 relative rate constants of radical 2d refer to radical 2e and vice versa as correctly stated in the Discussion. In the Experimental Section (Iodocyclization) read 2.25 g (8.86 mmol) of iodine instead of 2.25 g (1.10 mmol) of iodine.
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  • 54
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    Liebigs Annalen 1999 (1999), S. 527-538 
    ISSN: 1434-193X
    Keywords: Tris(pentafluorophenyl)borane ; Diarylborinic acid ; Arylboronic acid ; Chiral arylboron catalyst ; Lewis acid ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Arylboron compounds, ArnB(OH)3-n (n = 1-3), bearing electron-withdrawing aromatic groups such as triarylboranes, diarylborinic acids, and arylboronic acids represent a new class of air-stable and water-tolerant Lewis acid or Brønsted acid catalysts in organic synthesis. In particular, while tris(pentafluorophenyl)borane has primarily been used as a co-catalyst in metallocene-mediated olefin polymerization, its potential as a Lewis acid catalyst for organic transformation is now much more extensive. Diarylborinic acids and arylboronic acids have shown themselves to be powerful tools in the design of chiral boron catalysts. This article provides a comprehensive summary of the organic transformations catalyzed by arylboron compounds as acids.
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  • 55
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    Liebigs Annalen 1999 (1999), S. 573-577 
    ISSN: 1434-193X
    Keywords: Structure elucidation ; Constitutional analysis ; Natural products ; HMBC ; Computational chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The computer program COCON is introduced as a tool for the comprehensive structure elucidation of unknown organic compounds. In particular, structural proposals made on the basis of the molecular formula and of 2D-NMR experiments can be analyzed for the existence of alternative constitutions being in agreement with the same data set. The computational speed grounds on the evaluation of ambiguous long-range connectivity information during the process of structure generation. The data set experimentally obtained for the marine natural product oroidin (1) was selected, because proton-poor compounds usually cause uncertainties in NMR-based structure determinations. The calculation results encourage to move from the experience-based analysis of NMR chemical shifts or of MS fragmentations to the automated evaluation of routinely available connectivity information.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98241_s.pdf or from the author.
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  • 56
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    Liebigs Annalen 1999 (1999), S. 587-595 
    ISSN: 1434-193X
    Keywords: Phosphaalkenes ; Heterodiphospholes ; Cycloadditions ; Phosphaalkyne cyclooligomers ; Phosphorus-carbon cage compounds ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The first synthesis of a 1,2,4-oxadiphosphole 6 has been achieved by vacuum thermolysis of mesitylphosphaalkene 5. The novel heterocycle 6 exhibits an enormous potential for cycloaddition reactions, which predominantly proceed selectively at low temperatures. Compound 6 undergoes addition with two equivalents of phosphaalkynes 10 by a [4+2] cycloaddition/homo Diels-Alder reaction sequence to form novel oxatetraphosphadeltacyclenes 12 and 13. Tetrachloro-o-benzoquinone (14) undergoes a selective [4+1] cycloaddition with 12 and 13 leading to the spirocyclic products 15 and 16 containing λ5-phosphorus atoms. Treatment of the oxadiphosphole 6 with dimethyl acetylenedicarboxylate (17) provides the first access to a 1,2-oxaphosphole 18, which is formed after an initial [4+2] cycloaddition followed by a retro Diels-Alder reaction. An unexpected reaction of 6 is observed with tri-tert-butylazete (20) furnishing a new polycyclic system (→ 21).
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  • 57
    ISSN: 1434-193X
    Keywords: 1β-Methylcarbapenems ; Palladium ; Ruthenium ; Catalysis ; Cyclizations ; Stereoselective hydrogenation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -An efficient diastereoselective multi-step synthesis of bicyclic 1β-methylcarbapenem antibiotic precursors has been developed, starting from the commercially available 4-acetoxyazetidin-2-one 4. Chiral ruthenium catalysts are used in the hydrogenation step to control the β-stereochemistry at the 1-position, and a π-allylpalladium ring-closure strategy is used to form the functionalized carbapenem skeleton.
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  • 58
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    Liebigs Annalen 1999 (1999), S. 643-651 
    ISSN: 1434-193X
    Keywords: Oligomers ; Synthesis design ; Substituent effects ; Luminescence ; Cyclic voltammetry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Synthetic strategies towards appropriate symmetric and unsymmetric functionalization of the naphthalene ring are presented. By means of Knoevenagel and Wittig condensation reactions new fluorescent, differently functionalized oligo(2,6-naphthylenevinylene)s have been synthesized, the presence of terminal aldehyde or bromine substitution opening the way to the incorporation of the fluorescent trimers in a variety of polymeric materials. The effect of substituting the phenylene ring by the more bulky dialkoxynaphthalene system in arylenevinylene-type materials is studied from the structural point of view and the possibility to tune the emission color and the electron affinity through the introduction of naphthylenevinylene and cyano-substituted naphthylenevinylene units is also investigated.
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  • 59
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    Liebigs Annalen 1999 (1999), S. 661-664 
    ISSN: 1434-193X
    Keywords: Aziridines ; N-Heterocycles ; Fatty acids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The first successful preparation of the aziridines methyl cis-9,10;cis-12,13-diepiminooctadecanoate (3) derived from linoleic acid, and methyl cis-9,10;cis-12,13;cis-15,16-triepiminooctadecanoate (6) derived from linolenic acid, is reported. Remarkably, the bis- and trisaziridine were obtained in a reaction sequence that consists of only two steps, using technically pure methyl esters of epoxidized sunflower and linseed oil. The conversion of methyl 9,10;12,13-diepoxyoctadecanoate (1), with sodium azide and ammonium chloride in ethanol in the presence of water, yielded the new diazidodihydroxy compound methyl 9(10),12(13)-diazido-10(9),13(12)-dihydroxyoctadecanoate (2) in the first step. 2 was obtained as a regioisomeric mixture. The reaction of 2 with triphenylphosphane led to the bisaziridine 3. The analogous conversion of methyl 9,10;12,13;15,16-triepoxyoctadecanoate (4), via the new triazidotrihydroxy compound methyl 9(10),12(13),15(16)-triazido-10(9),13(12),16(15)-trihydroxyoctadecanoate (5), afforded trisaziridine 6.
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  • 60
    ISSN: 1434-193X
    Keywords: Cavitands ; Nuclear waste ; Actinide/lanthanide separation ; Solvent extraction ; Sulfur atoms ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Cavitands with phosphane sulfide moieties 4 and 8a,b were prepared in good yields from their phosphane oxide analogues, as more stable alternatives for the dithiophosphinic acids used at present. The cavitands 7a and 7b with flexible butoxyphosphane oxide ligating sites are more efficient than cavitand 3 having rigid methylphosphane oxide groups as was studied with EuIII picrate extractions. Due to the absence of an ionic functionality in the phosphane sulfides 4 and 8a,b AmIII and EuIII are not extracted, not even in the presence of synergents (e.g. TBP, TOPO, HDNNS). Cavitand 10 with phosphinic acid groups efficiently extracts EuIII in 1:1 or 2:1 complexes, depending on the metal-to-ligand concentration ratio (extraction constants Kex1 = 3.9·10-5M2 and Kex2 = 1.9·102M, respectively). Furthermore, in the case of 10 EuIII is preferentially extracted over AmIII with a separation factor SEu/Am up to 5.
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  • 61
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    Liebigs Annalen 1999 (1999), S. 691-696 
    ISSN: 1434-193X
    Keywords: Carbohydrates ; 4-Thiofuranosides ; Nucleosides ; Reaction mechanisms ; NOE measurements ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabino-furanose (9) has been prepared from D-xylose via the 1,4-dithio-L-arabino-furanoside 8. The crucial step of the reaction, i.e. the intramolecular cyclization of the open-chain dithioacetal 5, has been achieved in a yield of 90% by applying tetrabutylammonium iodide as promoter. Reaction of 9 with bis(trimethylsilyl)uracil or -thymine led to the benzyl derivatives 12 and 13 from which the deprotected 4′-thionucleoside analogues 14 and 15 have been prepared by debenzylation with boron tribromide.
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  • 62
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    Liebigs Annalen 1999 (1999), S. 737-750 
    ISSN: 1434-193X
    Keywords: Baeyer-Villiger oxidation ; Ketones ; Monopersulfate ; Peracids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -In the present review, we report the discovery of the formation of esters and lactones by oxidation of ketones with a peroxide derivative, namely the Baeyer-Villiger reaction. This reaction was first reported by Adolf von Baeyer and Victor Villiger a century ago in 1899, just one year after the oxidant they used (KHSO5) has been described. Furthermore, Baeyer and Villiger established the composition of this new inorganic peroxide and showed that its instability was the reason of a controversy between several European chemists between 1878 and 1893. For the first 50 years the mechanism of the Baeyer-Villiger reaction was a matter of debate. A side product, 1,2,4,5-tetraoxocyclohexane, was ruled out as an intermediate in the ester formation by Dilthey. Criegee postulated a nucleophilic attack of the oxidant on the carbonyl group. This mechanism was confirmed by von E. Doering by a labeling experiment with [18O]benzophenone. The rearrangement step occurs with retention of the stereochemistry at the migrating center. The competitive migration and the rate-determining step are also discussed in this review.
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  • 63
    ISSN: 1434-193X
    Keywords: Transglycosylation ; Glycosidases ; Thermus thermophilus ; Carbohydrates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The aim of this paper is to test the ability of a β-glycosidase from Thermus thermophilus to catalyse transglycosylation reactions in the presence of nitrophenyl glycosides as donors and other monosaccharides as acceptors. Our results show that this enzyme is able to induce such reactions either with nitrophenylgalactosides, -glucosides and -fucosides. With the two former donors, the autocondensation of the donor, which thus acts also as an acceptor, is faster than the transglycosylation with other acceptors. Furthermore, as the regioselectivity of the reactions is mainly of the β-[1→3] type, good yields are obtained for the synthesis of 2-nitrophenyl-β-D-galactopyranosyl-[1→3]-β-D-galactopyranoside and 2-nitrophenyl-β-D-glucopyranosyl-[1→3]-β-D-glucopyranoside. Conversely, in the presence of p-nitrophenylfucoside, the autocondensation is very limited, and with methyl-α-D-galactoside as an acceptor, the regioselectivity is mainly of the β-[1→6]-type resulting in the synthesis of methyl-β-D-fucopyranosyl-[1→6]-α-D-galactopyranoside.
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  • 64
    ISSN: 1434-193X
    Keywords: Monoynes ; Polyynes ; Alkali metals ; Liquid NH3 ; Hexamethylphosphoric triamide ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Efficient procedures have been developed for the stereospecific reduction by alkali metals of disubstituted acetylenes with long carbon chains. Acetylenes containing two or more (isolated) triple bonds are reduced considerably more easily than are monoynes.
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  • 65
    ISSN: 1434-193X
    Keywords: Aminophenols /Asymmetric synthesis ; C-C coupling ; Reductions ; Conformation analysis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enantiopure o-hydroxybenzylamines 2a-i were synthesized by diastereoselective reduction of the 2-imidoylphenols (R)-1a-i. Conformational analysis enabled the assignment of the absolute configurations of compounds 2a-i. The accessible o-hydroxybenzylamine (R,R)-2h serves as an effective catalyst precursor for highly enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes. This pathway represents a practical and operationally very simple methodology for the enantioselective synthesis of both the enantiomers of secondary alcohols 7a-f.
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  • 66
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    Liebigs Annalen 1999 (1999), S. 837-846 
    ISSN: 1434-193X
    Keywords: Friedel-Crafts reaction ; Hydroxyalkylation ; Aromatics ; Epoxides ; Zeolites ; Clays ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Solid acids, such as zeolites and clays, catalyse the intramolecular hydroxyalkylation (cyclialkylation) of several arylalkyl epoxides in moderate to excellent conversions and selectivities. The use of solid acids in these cyclialkylations provides a cleaner, better alternative to conventional Lewis and Brønsted acids, enabling a more facile workup of reaction mixtures and, in several cases, better selectivities.
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  • 67
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    Liebigs Annalen 1999 (1999), S. 861-868 
    ISSN: 1434-193X
    Keywords: Red phosphorus ; Phosphane PH3 ; Phosphorylations ; Ultrasound irradiation ; Redox chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The reactivity of red phosphorus towards aldehydes was investigated under basic and acidic media. It was demonstrated that the real phosphorylating agent involved in the reaction was phosphane (PH3) in basic media, and hypophosphorous acid (H3PO2) in acidic media. A convenient one-pot synthesis of (α-hydroxyalkyl)phosphinic acids from red phosphorus and aldehydes in basic media was realized under sonication. The same reaction under acidic media in the presence of hydriodic acid led to the corresponding phosphonic acids. The (α-hydroxyalkyl)phosphinic acids were readily prepared under sonication from hypophosphorous acid and aldehydes in the presence of catalytic amounts of hydrochloric acid. The mechanism of the addition reaction of PH3 to benzaldehyde was elucidated and shows the complexity of the reaction as a function of the experimental conditions.
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  • 68
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    Liebigs Annalen 1999 (1999), S. 909-915 
    ISSN: 1434-193X
    Keywords: Erythrina alkaloids ; Nitrogen heterocycles ; Nitro aldol reaction ; Michael addition ; Pummerer reaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A successful new strategy for the synthesis of erythrinanes is reported. (Nitromethyl)arene derivative 16 was condensed with aldehyde 17 to give nitro aldol 19. After removal of the hydroxy group, the subunits 26a,b, containing the erythrinane rings A and D, were formed by intramolecular Michael addition. Reduction of the nitro function, followed by cyclization of the resulting amino group with the appended acetate group afforded the bicyclic lactams 29a,b, bearing an angular aryl group. Two-carbon elongation at the nitrogen atoms of 29a and 29b by means of hetero Michael addition of methyl phenyl sulfoxide, followed by Pummerer-type cyclization, gave cis- and trans-11-phenylthioerythrinan-8-ones 35a and 35b, respectively. Reductive desulfurization at C-11 furnished the desired erythrinan-8-ones 39a and 39b in 8 steps from 16.
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  • 69
    ISSN: 1434-193X
    Keywords: Crystal engineering ; Diynes ; Photochemistry ; Solid-state chemistry ; Polymers ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diynes 4a-c were obtained from the corresponding 2,5-dimethoxybenzenes 1 by bromination followed by a copper-catalyzed Grignard reaction with 3-bromoprop-1-yne. Catalyzed coupling of the resulting 3-(2,5-dimethoxyphenyl)prop-1-ynes 3 under Hay conditions gave the hexa-2,4-diynes 4a-c in good yields. The molecular structures of the diynes 4a and 4b were determined by X-ray diffraction analysis. In each crystal structure, an unusual 1,6-synperiplanar conformation of the hexa-2,4-diyne unit is observed, with the 1,6-diphenyl substituents arranged in a coplanar orientation. According to the crystal structure data obtained, irradiation of diynes 4a and 4b afforded the deeply-colored, highly-ordered polymers 5a and 5b under topochemical control. Oxidation of 4a and 4b with cerium(IV) ammonium nitrate gave the corresponding 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diyne-1,6-diones 6a and 6b.
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  • 70
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    Liebigs Annalen 1999 (1999), S. 931-936 
    ISSN: 1434-193X
    Keywords: Nucleosides ; Phosphonates ; Nucleophilic additions ; C-C coupling ; Reduction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Acyclic carba-nucleoside phosphonates, modelled on natural deoxyribonucleotides have been prepared starting from DNA nucleobases and tert-butyl acrylate. The products obtained from a Michael-type reaction were elongated to β-oxo esters that were first reduced to β-hydroxy esters and then transformed into protected β-hydroxy aldehydes. Wittig-Horner-Emmons reaction with the anion of tetraisopropyl methylenebisphosphonate gave, after deprotection, the desired 4-hydroxy-6-purinyl- or -6-pyrimidinyl-1-hexenylphosphonic acids. A dimer, potential precursor of acyclic polynucleotides (APN), homomorphous with DNA, was also prepared.
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  • 71
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    Liebigs Annalen 1999 (1999), S. 955-958 
    ISSN: 1434-193X
    Keywords: Tetraethylammonium peroxydicarbonate ; Tetraethylammonium carbonate ; N-alkylated pyrroles ; Electrochemistry ; Electrogenerated bases ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Electrochemically generated tetraethylammonium peroxydicarbonate (TEAPC) and tetraethylammonium carbonate (TEAC) react under very mild conditions with pyrroles affording, after addition of a suitable alkylating agent, the corresponding N-alkylated pyrroles in high yields. C-Alkylated pyrroles have not been isolated in any case reported.
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  • 72
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    Liebigs Annalen 1999 (1999), S. 979-980 
    ISSN: 1434-193X
    Keywords: Ketones ; Myxobacterium ; Pheromones ; Stigmatellaaurantiaca ; Stigmolone ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The racemic myxobacterial pheromone (±)-1 (stigmolone), which induces the formation of the fruiting body of Stigmatellaaurantiaca, was synthesized from methyl isobutyl ketone (2) in 48% overall yield in four steps
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  • 73
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    Liebigs Annalen 1999 (1999), S. 1005-1009 
    ISSN: 1434-193X
    Keywords: Hydrogen migration ; Anthronylidene ; Quinone methide ; Matrix isolation ; Photochemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The photochemistry of 4-methyl-9,10-diazoanthrone (7a) and 1,4-dimethyl-9,10-diazoanthrone (7b) was investigated in argon matrices at 10 K. Visible-light irradiation results in the formation of the anthronylidenes 5a and b, respectively, which were identified by oxygen trapping, by comparison of the IR and UV/Vis spectra with that of the parent anthronylidene 6, and by comparison of the IR spectrum with that calculated by DFT methods. The carbenes 5 are thermally stable under the conditions of matrix isolation; however, irradiation with visible or UV light results in the rearrangement to the quinone methides 10a and b.
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  • 74
    ISSN: 1434-193X
    Keywords: Sulfoximines ; Oxabicyclic ethers ; Asymmetric synthesis ; Euglobal ; Arenaran ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -2-Cyclopentenyl- and 2-cyclohexenylmethyl sulfoximines can be converted into angular carbon-functionalised, highly substituted, isomerically pure (ds ≥ 98%) 2-oxabicyclo[3.3.0]octanes and 2-oxabicyclo[3.4.0]nonanes in high yields by a convenient one-pot sequence. Molecular frameworks such as these can be found in many biologically active natural products. In addition to the methodological work, we report on studies towards the total synthesis of the euglobals G1 and G2 and arenaran A.
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  • 75
    ISSN: 1434-193X
    Keywords: Phosphaalkynes ; Cycloadditions ; Polycycles ; Cage compounds ; λ3-Phosphinines ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Phosphaalkynes 2 and electron-deficient alkynes 11 readily react in a [4 + 2] cycloaddition process with 5,8-bis(trimethylsilyl)cycloocta-1,3,6-triene (8) in its bicyclic form 10 to furnish regioselectively the tricyclodecadienes 12 and 13, respectively. The phosphorus-containing compounds 12 exhibit structural features which make them suitable for homo-Diels-Alder reactions with electron-deficient acetylenes. A single crystal structure analysis of the homo-Diels-Alder adduct 14b confirmed the structure and relative configuration of the phophatricyclodecadienes 12. In solution the tricyclodecadienes 13 are prone to facile cycloreversion yielding the phthalic esters 15 and the cyclobutene 16. The latter is rapidly converted into the corresponding 1,3-butadiene 18, which can be trapped in a Diels-Alder/phospha-ene/Diels-Alder tandem reaction sequence by phosphaalkyne 2a. The phosphatricyclodecadiene 12 is thermally more stable; loss of cyclobutene 16 only occurs under FVP conditions to afford the λ3-phosphinine 22.
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  • 76
    ISSN: 1434-193X
    Keywords: Asymmetric synthesis ; Chiral synthons ; P-(o-Hydroxyaryl)diazaphospholidine P-oxides ; Rearrangements ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The totally regio- and stereoselective P-O-to-P-C rearrangement in the synthesis of various chiral P-(o-hydroxyaryl)diazaphospholidine P-oxides has been investigated. This reaction proceeds with excellent yields ranging from 72 to 92%, total retention of configuration at the phosphorus atom, and complete regioselectivity. An exception was found with naphthyl derivatives, which gave mixtures of two regioisomers. In all cases, the products generated have been unambiguously characterized by 1H-, 13C-, and 31P-NMR spectroscopy as well as by X-ray-diffraction analysis.
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  • 77
    ISSN: 1434-193X
    Keywords: Cyclocarbonylation ; Alkynes ; Catalysis ; Palladium ; Vinyl triflates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -o-Ethynylphenols react with vinyl triflates, in the presence of tetrakis(triphenylphosphane)palladium(0) and under carbon monoxide, to form 3-alkylidene-2-coumaranones in good yield.
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  • 78
    ISSN: 1434-193X
    Keywords: Sulfur-linked thiooligosaccharides ; Oligosaccharin thio analogs ; Phytoalexin elicitor thio analogs ; Soybean glucan-binding assays ; Structure-activity relationships ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The sulfur-linked pentathiohexasaccharide 3I,3IV-di-β-D-glucopyranosylthiogentiotetraose (12) has been prepared by a convergent approach involving the reaction of 1,2,4-tri-O-acetyl-6-deoxy-6-iodo-3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thio-β-D-glucopyranose (10) with the sodium salt of 2,3,4-tri-O-acetyl-6-S-[2,4-di-O-acetyl-3,6-di-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,6-dithio-β-D-glucopyranosyl]-1,6-dithio-β-D-glucopyranose (4). A further reaction, involving the sodium salt of the peracetylated β-1-thio derivative of 12 with 1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose (26), afforded the homologous sulfur-linked hexathioheptasaccharide 3II,3V-di-β-D-glucopyranosylthiogentiopentaose (28). Related sulfur-linked positional isomers 3II,3IV-di-D-β-glucopyranosylthiogentiotetraose (34) and 3III,3V-di-β-D-glucopyranosylthiogentiopentaose (39) have been prepared using analogous synthetic strategies. Thus, SN2 displacement of the iodine atom in 10 by the sodium salt of 2,4-di-O-acetyl-3,6-di-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,3,6-trithio-β-D-glucopyranose afforded a tetrathiopentasaccharide, which resulted in the pentathiohexasaccharide 34 by a sequence of reactions involving the 1-thioglycose 32 in reaction with 26. The hexathioheptasaccharide 39 was obtained conveniently by the reaction of 26 with the acetylated 1-thio-6I, 3II, 6II, 3IV, 6IV-pentathio derivative 37, followed by deacylation. The four isomeric pentathiohexa- and hexathioheptasaccharides 12,34 and 28,39, respectively, were all found to be active in eliciting phytoalexin accumulation in soybean cotyledon tissue and in binding to a glucan-binding protein of soybean, although to a lesser extent than the corresponding O-oligosaccharides, the alternate thiohexa- and thioheptasaccharides 12,28 being more active as compared to the geminally branched isomers 34,39.
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  • 79
    ISSN: 1434-193X
    Keywords: Pyrolysis ; Ring contraction-ring expansion ; Rearrangements ; Homolytic scission ; IGLOIII//6-31G ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Flash vacuum thermolysis (FVT, 1000 °C ≥ T ≥ 1200 °C) of acenaphtho[1,2-a]acenaphthylene (3, C22H12) gave the C22H12 cyclopenta-fused polycyclic aromatic hydrocarbon (CP-PAH) acenaphtho[1,2-e]acenaphthylene (4), cyclopenta[cd]perylene (5) and cyclopenta[def]benzo[hi]chrysene (6). Whereas the formation of 4 is explained by a ring contraction/ring expansion rearrangement of 3, the identification of 5 and 6 suggests that 3 also undergoes homolytic scission of a five-membered ring's Carbon-Carbon single bond furnishing the transient diradical intermediate 7. Ring closure of 7to form 8 after rotation around the Carbon-Carbon single bond of the intact five-membered ring followed by hydrogen shifts will give 6. The latter can rearrange subsequently into 5by ring contraction/ring expansion. The structural assignment of 4 and 5 was supported by independent FVT of 6,12-bis(1-chloroethenyl)chrysene (14) and 3-(1-chloroethenyl)perylene (23), respectively. FVT of 14 (900-1200 °C) gave in a consecutive process 6,12-bis(ethynyl)chrysene (15), 9-ethynylbenz[j]acephenanthrylene (16) and bis(cyclopenta[hi,qr])chrysene (17). Although at T ≥ 900 °C 17 selectively rearranges into 4 by ring contraction/ring expansion, at 1200 °C the latter is converted into 5 presumably via a diradical intermediate obtained by homolytic scission of a single Carbon-Carbon bond of a five-membered ring. FVT of 23 gave in situ 3-ethynylperylene (25), which at 1000 °C is nearly quantitatively converted into 5. The propensity of internal cyclopenta moieties to undergo homolytic scission of a five-membered ring′s Carbon-Carbon single bond was corroborated by independent FVT of benzo[k]- (11) and benzo[j]fluoranthene (12). Previously unknown thermal pathways to important (CP)-PAH combustion effluents are disclosed at T ≥ 1000 °C.
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  • 80
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    Liebigs Annalen 1999 (1999), S. 1233-1238 
    ISSN: 1434-193X
    Keywords: Electrophilic additions ; Bromine addition to double bonds ; Hydrogenation of double bonds ; Rotaxanes ; Supramolecular chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Here we report on the possibility of using rotaxane wheels as noncovalent protecting groups which significantly decrease the activity of functional groups in the central part of the axle. The amide-linked rotaxanes 5aand 5b, each containing a C=C double bond in their axle, have been synthesised. The catalytic hydrogenation of these two rotaxanes proceeds slower than those of the corresponding free axle compounds 6a and 6b, indicating steric hindrance of the C=C double bond by the wheel of the rotaxane in each case. Nontheless, the rotaxane 9with an aliphatic (succinic acid) middle region in its axle can be prepared in this manner. Dehydrobromination of the axle in the rotaxane 15yields the rotaxane 16 with a C≡C triple bond located in the centre of the axle.
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  • 81
    ISSN: 1434-193X
    Keywords: Cage compounds ; Cubanes ; Donor-acceptor systems ; Solid-state structures ; Substituent effects ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The crystal structures of methyl 4-methoxycubane-1-carboxylate (1), 1-acetamido-4-fluorocubane (2), methyl 4-acetoxycubane-1-carboxylate (3), 1,4-difluorocubane (4), 1,4-dichlorocubane (5), and N,N-diisopropylcubane-1,4-dicarboxamide (6) have been investigated by means of X-ray diffraction analysis. Fluorine and chlorine substituents cause a shortening of the vicinal bonds, as is seen in the 4-halocubane-1-carboxylates. The cage bonds vicinal to the ester substituent, with a favorable orientation with regard to the π-acceptor influence of this group become longer than the CH-CH bonds. Furthermore, the influence on bond length with respect to the orientation of this group relative to bonds within the cubane skeleton has been investigated experimentally. The effect of the methoxy group has also been found to depend on the orientation. The cage bond antiperiplanar to the methyl group is shortened, while the cage bonds in gauche orientation to this group are lengthened. As seen in the case of the halogen-substituted derivatives, the bonds bearing the acetoxy substituent are shortened due to the σ-acceptor property of this group. Ab initio calculations on compounds 1, 2, 4, and 5 performed at the 6-31G* level confirm the experimental results.
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  • 82
    ISSN: 1434-193X
    Keywords: Catenanes ; Mechanically interlocked molecules ; Molecular recognition ; Rotaxanes ; Template-directed synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane - i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable-temperature 1H-NMR spectroscopy.
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  • 83
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    Liebigs Annalen 1999 (1999), S. 1057-1073 
    ISSN: 1434-193X
    Keywords: Free radicals ; Stereoselective addition ; Chiral 1,3-dioxin-4-ones ; Photoreactions ; Spirocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Intermolecular addition of radicals to the 1,3-dioxin-4-ones 1a,b and 2a,b with (-)-menthone incorporated as chiral auxiliary in 2-position were investigated. Photochemically generated radicals from 1,3-dioxolane, oxolane, and 2-propanol were added with high facial selectivity from the more exposed a-side. Intramolecular addition of 1,3-dioxolan-2-yl radicals to chiral dioxinones proceeded less efficiently and with lower selectivity also from the a-side. Nevertheless, it was possible to form the new spirocyclic compounds 22-27. The 1,3-dioxin-4-ones 32a,b possessing an unsaturated side chain were attacked by radicals at the terminal double bond. In the case of irradiation of 32b in 1,3-dioxolane a cyclization followed the intermolecular addition of a 1,3-dioxolan-2-yl radical and the dispiro compound 36 was formed. However, the formation of dispiro compound 40 required two reaction steps starting with irradiation of 32b and bromotrichloromethane. The achiral 1,3-dioxin-4-one 44 possessing an unsaturated side chain at C-2 was attacked by 1,3-dioxolan-2-yl radicals preferentially at C-6.
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  • 84
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    Liebigs Annalen 1999 (1999), S. 1075-1084 
    ISSN: 1434-193X
    Keywords: Asymmetric synthesis ; Atropisomerism ; Bis(hydroxylation) ; Conformational analysis ; Palladium ; Vitamin E ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Several new approaches for the enantioselective synthesis of the chromane moiety of vitamin E are described. Sonogashira coupling of 3a with the alkyne 4 and subsequent elimination gave 6, which was bis(hydroxylated) in 93% yield and with 85% ee. Recrystallization gave enantiopure 7a, which was hydrogenated and transformed into the vitamin E precursor 11. The bis(hydroxylation) of 18 and 21 to give 9 and 22, respectively, was less than satisfactory, proceeding with ee values of 28% and 18%. In contrast, stereoselective allylation of ketone 15 followed by removal of the protecting group or ozonolysis of the allyl moiety furnished the allyl alcohol 26 and the aldehyde 27, respectively, in almost enantiopure form, which again could be used as precursors for vitamin E. Partial hydrogenation of 5a gave the alkene 32a and that of 28 the alkene 30b, both of which show interesting atropisomerism.
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  • 85
    ISSN: 1434-193X
    Keywords: Clathrate hosts ; Clathrates ; Crystalline inclusion compounds ; Clathrate structures ; Host-guest chemistry ; Anthracene derivatives ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A series of new clathrate host molecules (1-10) containing two diarylhydroxymethyl groups attached to different positions (1,5 or 1,8) of a basic anthracene construction unit have been synthesized. Their clathrate formation properties with a variety of organic guests, including amines, alcohols, ketones, and other dipolar aprotic compounds or aromatic hydrocarbons are reported (143 examples of clathrates). The inclusion properties and the clathrate stoichiometries depend in a systematic manner on the structure of the host molecules. The crystal structures of six selected clathrates of different classes of compound have been determined by X-ray diffraction.
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  • 86
    ISSN: 1434-193X
    Keywords: Carbohydrates ; Glycals, nitro ; Michael additions ; Glycosylations ; Glycosides, galactosamine ; Reduction, nitro group ; Glycopeptides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Michael addition of serine and threonine derivatives 4a-4c to 3,4,6-tri-O-benzyl-2-nitro-D-galactal (1) afforded the corresponding 2-deoxy-2-nitro-α-D-galactopyranosides 5a-5c in good yield and stereoselectivity. 2-deoxy-2-nitroglycosides 5a and 5b were reduced to the 2-acetamido compounds by platinized Raney nickel T4. Manipulation of the protecting groups afforded known N-Fmoc-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine (8a) and -threonine (8b), valuable building blocks for O-glycopeptide synthesis.
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  • 87
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    Liebigs Annalen 1999 (1999), S. 1173-1183 
    ISSN: 1434-193X
    Keywords: Marine alkaloids ; Pyrroloquinoline ; Total synthesis ; Heterocycles ; Alkaloids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Batzellines A and B (1a, b) and isobatzellines A and B (2a, b) are 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline-containing marine alkaloids characterized by the presence of a methylthio substituent at C-2 of the tricyclic system. We describe here the total synthesis of these natural compounds following the synthetic strategy that we have used previously for the synthesis of damirones A and B, batzelline C, isobatzelline C, discorhabdin C, and makaluvamines A, B, C, and D. The introduction of the methylthio group by electrophilic substitution of a pyrrolo[4,3,2-de]quinoline, appropriately substituted and in a suitable oxidation state, is the key step in the success of these syntheses.
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  • 88
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    Liebigs Annalen 1999 (1999), S. 1213-1221 
    ISSN: 1434-193X
    Keywords: Diazo compounds ; Carbenes ; Carbenoids ; Silicon ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Copper(I) triflate catalyzes the transformation of α-[(2-alkynyl)oxy]silyl-α-diazoacetates 1a-g into 1,2-bis(2,5-dihydro-1,2-oxasilol-4-yl)ethenes 2 and/or 2H-1,2-oxasilines 3. With rhodium(II) perfluorobutyrate as catalyst, 1a-e furnish only 3 but no 2. Bicyclic 2-methoxyfurans 6 are formed when 1a,c,e (containing terminal alkyne functions) are treated with catalytic amounts of copper(I) chloride. The experimental observations are explained in terms of metal-mediated intramolecular cyclopropenation and subsequent metal-assisted ring-opening of the strained bicyclic cyclopropene leading to vinylcarbene-metal complexes. An unusual autoxidation of 2H-1,2-oxasilines 3a,c,e is also described.
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  • 89
    ISSN: 1434-193X
    Keywords: Pheromones ; Aspidiotus nerii ; Sex attractant ; Cyclobutane ; Enantiomeric purity ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Synthesis of both enantiomers of the Aspidiotus nerii sex pheromone and their diastereomers has been achieved using, as a key step, an intramolecular ester enolate alkylation reaction for the formation of the cyclobutane ring with a good control of the relative configurations of the asymmetric centers. Stereoselective synthesis of a number of other trisubstituted cyclobutane derivatives also proves the versatility of the methodology used for the synthesis of the Aspidiotus nerii sex pheromone.
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  • 90
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    Liebigs Annalen 1999 (1999), S. 1249-1252 
    ISSN: 1434-193X
    Keywords: Amino alcohols ; Amine N-oxides ; Asymmetric synthesis ; Hydrogen bonds ; Structure determination ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enantiopure 2-azabicyclo[3.3.0]octanes 1a-d and ent-1e were oxidized with mCPBA to provide either diastereomeric pairs of N-oxides (2a/3a and 2b/3b) or diastereomerically pure compounds (2c,d and ent-2e). The structure of compounds 2a and ent-2e was confirmed by an X-ray study. The factors that affect the oxidation process are discussed.
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  • 91
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    Liebigs Annalen 1999 (1999), S. 1595-1600 
    ISSN: 1434-193X
    Keywords: Photochemistry ; Anthracenes ; Fluorescence spectroscopy ; Cycloaddition reactions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The novel 2,6-donor-acceptor-substituted anthracene, namely 6-methoxy-2-anthracene carboxylic acid (7), was synthesized. The emission of this compound exhibits significant solvatochromism. The fluorescence band position and intensity are also remarkably sensitive to H+. Irradiation of the anthracene 7 in solution yields the syn and anti head-to-tail dimers exclusively. A synergistic electronic effect between the donor and acceptor substituents is proposed to operate on the photophysical and photochemical properties of anthracene 7.
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  • 92
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    Liebigs Annalen 1999 (1999), S. 1601-1609 
    ISSN: 1434-193X
    Keywords: Photoelectron spectroscopy ; Conformation analysis ; Ab initio calculations ; Through-space interactions ; NMR spectroscopy ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The dioximes 4-6 and the dimethoximes 7-9, which contain the functional groups in opposite positions of a six-, eight-, or ten-membered ring, were synthesized. Their conformational properties and transannular interactions were investigated by spectroscopic (PE, 13C NMR) and theoretical (MMX, AM1, ab initio HF, and B3LYP) methods. While the cyclooctane derivatives 5 and 8 have conformations favourable for through-space interactions of the π(C=N) orbitals, in the other compounds no such interactions can be ascertained. Through-space orbital interactions in the molecules with an eight-membered ring lead to a splitting of the π(C=N) MOs of 0.4 eV.
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  • 93
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    Liebigs Annalen 1999 (1999), S. 1611-1617 
    ISSN: 1434-193X
    Keywords: Photoelectron spectroscopy ; Conformation analysis ; Ab initio calculations ; Through-space interactions ; NMR spectroscopy ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bicyclic dioximes 4-6 and dimethoximes 7-9, which contain the functional groups in opposite positions of bridged eight-membered rings, were synthesized. Their conformational properties and transannular interactions were investigated by spectroscopic (PE, 13C NMR) and theoretical (MMX, AM1, ab initio HF, and B3LYP) methods. While in the 3,7-disubstituted bicyclo[3.3.1]nonane derivatives 5 and 8 the eight-membered ring has a CC conformation favourable for through-space interactions of the π(C=N) orbitals, in the bicyclo[3.3.0]octane derivatives 4 and 7 as well as the 2,6-disubstituted bicyclo[3.3.1]nonanes 6 and 9 the functional groups are in geometric orientations that are unfavourable for such interactions. Through-space orbital interactions in the molecules with favourable conformations lead to a splitting of the π(C=N) MOs of 0.4-0.6 eV.
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  • 94
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    Liebigs Annalen 1999 (1999), S. 1653-1663 
    ISSN: 1434-193X
    Keywords: Planar chirality ; Cyclophanes ; Configuration determination ; NMR spectroscopy ; Diastereomers ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of compounds Q2Z was prepared, where Q = [2.2]paracyclophan-4-yl and Z = C(=O) (4), CH2 (5), SiMe2 (6), S (7), P(=O)OMe (8), and C(=O)C(=O) (9). Because of the planar chirality of Q, these compounds occur as meso- (m) and chiral (c) diastereomers, which were formed in equal amounts. They were separated in the cases of 4-7 and enriched in the case of 9 (diastereomeric ratio ca. 7:3). Compound 8 possesses a pseudoasymmetric phosphorus centre and occurs as one chiral (8c) and two meso diastereomers (8m1, 8m2), all three of which were isolated separately. The configurations of 5m/5c, 6m/6c, and 8c were directly determined by NMR spectroscopy, that of 4m/4c indirectly by reducing the separated compounds to 5m and 5c, respectively, and that of 7m by X-ray diffraction. The favoured conformations of 4-8 were studied by molecular mechanics computations by using the MM3(94) program. An attempt was made to rationalize some chemical shift differences between diastereomers on the basis of the conformers predicted.
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  • 95
    ISSN: 1434-193X
    Keywords: 2,2′-Bipyrazine reactivity ; Experimental electron density distribution ; High-resolution X-ray diffraction ; Electron density topology ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The synthesis and reactivity of mono- and bis(chloromethyl)-2,2′-bipyrazines toward nucleophiles are reported. The reactivity of the bipyrazine ring is explained in terms of allylic substitution and rearrangement mechanisms. A new family of monofunctionalized bipyrazine derivatives as molecular building blocks for supermolecules has been obtained, opening access to unsymmetrical ligands. The low-temperature crystallographic structure and the experimental electron density distribution of 6,6′-bis(chloromethyl)-2,2′-bipyrazine have been determined on the basis of high-resolution X-ray diffraction data. The electron density of the molecule has been accurately analyzed using the topological properties of its gradient and Laplacian features. The reactivity of these bidentate molecules in metal complexation is related to the shape of the atomic basins and may be explained in terms of a key/lock-type interaction. The results are compared with corresponding data for 2,2′-dimethyl-6,6′-diphenyl-4,4′-bipyrimidine.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98532_s.pdf or from the author.
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  • 96
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    Liebigs Annalen 1999 (1999), S. 1507-1515 
    ISSN: 1434-193X
    Keywords: Ketones ; Sulfoxides ; Phenols ; Steric hindrance ; Acidity ; Basicity ; NMR spectroscopy ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The proton-transfer equilibrium of several bases and acids, including some sterically hindered ketones, sulfoxides, and phenols, has been investigated by means of the determination of the thermodynamics of the equilibrium, NMR 13C relaxation measurements, and quantum chemical calculations. The analysis of such data yields information about the steric effects on basicity or acidity and about the underlying reasons for the anomalous behavior of species having a sterically hindered basic or acidic site. Thus, it is demonstrated that the anomalously low basicity of two sterically hindered ketones (tBu2CO and PhCOtBu) is enthalpic in origin and stems from steric hindrance to the solvation of their protonated forms. No such effect is found for analogous sulfoxides, whereas phenols display a more complex behavior.Supporting information for this article is available on the WWW under //http://www.wiley-vch.de/contents/jc_2046/1999/99105_s.pdf or from the author.
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  • 97
    ISSN: 1434-193X
    Keywords: 1,3-Dipolar cycloadditions ; Diphenyldiazomethane ; N-Alkyloxycarbonyl-N-(2,2,2-trichloroethylidene)-amines ; Δ3-1,3,4-Triazoline ; Aziridines ; 2-Azadiene ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of the title imines with diphenyldiazomethane gives a Δ3-1,3,4-triazoline, which leads, after loss of dinitrogen, to a transient azomethine ylide. Subsequent elimination of ethyl or methyl chloroformate gives the unexpected 1,1-diphenyl-4,4-dichloro-2-aza-1,3-butadiene.
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  • 98
    ISSN: 1434-193X
    Keywords: 3,4-Disubstituted pyrroles ; Porphyrin octaesters ; Liquid crystals ; π-π interactions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new and efficient method of preparing 3,4-pyrrolediacetic esters 3 is reported, together with their conversion, according to the Lindsey procedure, to a series of octa- and dodeca-substituted porphyrins. This procedure, which consists of a palladium-catalysed oxidative alkoxycarbonylation of N-substituted dipropargylamine derivatives 1, works nicely for n-alkyl alcohols in the range C1 to C14. The thermotropic behaviour of this series of porphyrins (28 compounds) has been investigated using polarization microscopy, DSC, X-ray diffraction, and miscibility tests. The planarity of the macrocyclic core constitutes the major structural requirement for mesophase formation. The mesophase temperature range is controlled by the length of the side chains through the melting point and by the strength of π-π interactions among the cores through the clearing point. The same set of rules governing porphyrin packing in the solid state can be employed to predict mesophase formation and organization in porphyrin octaesters
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  • 99
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    Liebigs Annalen 1999 (1999), S. 1921-1924 
    ISSN: 1434-193X
    Keywords: Cyclizations ; Electrocyclic reactions ; Solvent effects ; Salt effect ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The rate constants of the electrocyclic ring closure of (1Z,3Z,5E)-1,2,6-triphenylhexa-1,3,5-triene (1) and of the ring opening of dimethyl 3,4-dimethyl-1,2-diphenylcyclobutene-cis-3,4-dicarboxylate (3) were determined in 15 and 16 solvents, respectively. The ring closure of 1 shows, in spite of theoretical predictions, neither solvent nor salt effects. For the ring opening of 3, small solvent and salt effects were found, suggesting the possibility of observing small acceleration due to specific solute-solvent or salt interactions.
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  • 100
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    Liebigs Annalen 1999 (1999), S. 1925-1933 
    ISSN: 1434-193X
    Keywords: γ-Lycorane ; Radicals ; Cyclizations ; Natural products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (±)-γ-Lycorane has been synthesized in ten steps from piperonylic alcohol. Two radical reactions were used successively to build the D and B rings. A formal synthesis of (+)-γ-lycorane was achieved via an optically active unsaturated aldehyde intermediate.
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