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  • 1
    Digitale Medien
    Digitale Medien
    Pyrrolo[1,2-b]cinnolin-6,8-dicarbonsäure-diethylester: Produkt einer anomalen Vilsmeier-Reaktion (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 627-630 
    Details
    ISSN: 0170-2041
    Schlagwort(e): Vilsmeier reaction, anomalous ; Pyrrolo[1,2-b]cinnoline, derivative ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Diethyl Pyrrolo[1,2-b]cinnoline-6,8-dicarboxylate, a Product of an Anomalous Vilsmeier ReactionA byproduct of the Vilsmeier reaction of 1 has been shown by X-ray structure determination to be the pyrrolo[1,2-b]cinnoline 3. Informations concerning the mechanism of formation of 3 have been obtained from labeling experiments and an unequivocal assignment of NMR spectra.
    Zusätzliches Material: 5 Tab.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.1990199001120
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  • 2
    Digitale Medien
    Digitale Medien
    1,3-Dioxycyclopentadienes from (1-Alkynyl)carbene Tungsten Complexes - Domino Cyclization/Cycloaddition Reactions (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1183-1192 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Carbene complexes ; 1-Metallahexatrienes ; Cyclopentadienes ; Carbene complexes ; Tungsten ; Domino cyclization ; Pentalenes ; Spirocyclopentanes ; Spiro compounds ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: -1,3-Dioxytetrahydropentalenes 9 have been generated by base-catalyzed addition of protic oxygen nucleophiles ROH 6a-g (RO = carboxy or phenyloxy) to the [2-(1-cyclopentenyl)ethynyl]carbene tungsten complex 3. Compounds 9 are highly reactive and afford (cyclobutenyl)carbene complexes 12a-g through spontaneous [2+2] cycloaddition to a second molecule of the (1-alkynyl)carbene complex 3. Thermolysis of compounds 12 was found to generate indeno[b]-spiro-tricyclo[5.3.0.0]decadienes 18 through π-cyclization of the 1-tungsta-1,3,5-hexatriene unit involving insertion of carbon monoxide into the W—C bond.
    Zusätzliches Material: 3 Ill.
    Materialart: Digitale Medien
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  • 3
    Digitale Medien
    Digitale Medien
    A General Route to the Monomeric Subunits of the Macrotetrolides - A Short Synthesis of Methyl Nonactate (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 2073-2078 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Sultones ; Intramolecular Diels-Alder reaction ; Desulfurization ; Heterocycles ; Actic acids ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: A highly stereoselective and flexible sultone route to actic acids, the monomeric subunits of the macrotetrolides, has been developed and exemplified for nonactic acid (2a). Due to the extensive application of tandem transformations, only six steps were needed to secure methyl nonactate (20) from furan.
    Materialart: Digitale Medien
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  • 4
    Digitale Medien
    Digitale Medien
    Structural and Spectroscopic Evidence for the Occurrence of gauche-Betaine Intermediates in the Thio Wittig Reaction (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1831-1841 
    Details
    ISSN: 1434-193X
    Schlagwort(e): Ylides ; Wittig olefination ; Reaction mechanism ; Phosphorus-carbon coupling constants ; Substituent perturbation ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Reaction of the ylide (cyclopropyl)3P=CH2 with Michler's thioketone S=C(C6H4NMe2)2 in [D5]pyridine gave the thio Wittig intermediate [(cyclopropyl)3P+-CH2-CAr2-S-] (11; 31P NMR: δ = +27.7). Compound 11 was characterized by X-ray diffraction and shown to exhibit a gauche-betaine-type structure with an S-C-C-P dihedral angle of 52.9(3)° and a P···S separation of 3.312(2) Å. The characteristic averaged 1JPCipso(aryl) coupling constant was used to elucidate the characteristic structural properties of Wittig and thio Wittig intermediates derived by treatment of the series Ph3P=CH2 (2a), Ph2MeP=CH2 (2b), and PhMe2P=CH2 (2c) with bis(p-methoxyphenyl) ketone to give 3 or benzophenone (to give 3′) or bis(p-methoxyphenyl) thioketone (to give 5), respectively. The oxaphosphetane series 3′a-3′c shows a strong response of the 1JPCipso(aryl) values (3a: 94 Hz; 3′b: 74 Hz; 3′c: 47 Hz) to this substituent perturbation, as it is expected for a dynamic trigonal-bipyramidal situation at the phosphorus atom, whereas the thio Wittig intermediate is only very little affected [1JPCipso(aryl) of 5a: 92 Hz; 5b: 86 Hz; 5c: 82 Hz]. Thus, the thio Wittig intermediates 5 seem to exhibit a pronounced phosphonium character in polar solvents and may be regarded as thiabetaine-type intermediates in solution.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
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  • 5
    Digitale Medien
    Digitale Medien
    Regioselectivity of Oxysulfenylations of Cycloocta-1,5-diene (1998)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 340 (1998), S. 455-458 
    Details
    ISSN: 0941-1216
    Schlagwort(e): Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: The regioselectivity of transannular O-heterocyclization of cycloocta-1,5-diene (1) with phenylsulfenyl chloride and methanol or water, respectively, is determined by the oxy-component which acts as nucleophilic partner in the electrophilic three component reaction. The thermodynamically more stable endo, endo-2,6-bis(phenylsulfenyl)-9-oxabicyclo[3.3.1]nonane (2) is formed almost exclusively in methanol while the isomeric 9-oxabicyclo[4.2.1]nonane (3) is favored under kinetic control in the presence of water. The oxidation of 2 or 3 yields the bissulfones 4 and 5, respectively.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/prac.19983400508
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  • 6
    Digitale Medien
    Digitale Medien
    Hydrazinüberbrückte Annulene, 7. Synthese von 6H-9b,9c-Diazacyclopenta[cd]phenalen-5,7-dicarbonsäure-diethylester (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 623-625 
    Details
    ISSN: 0170-2041
    Schlagwort(e): Annulenes, hydrazino-bridged ; Vilsmeier formylation ; Pi systems, unstable ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Hydrazino-Bridged Annulenes, 7.  -  Synthesis of Diethyl 6H-9b,9c-Diazacyclopenta[cd]phenalene-5,7-dicarboxylateThe 1,4-dihydropyridine 4 has been obtained from 1-amino-pyrrole and diethyl 2,6-dioxo-3,5-heptanedicarboxylate. Subsequent Vilsmeier reaction led to the aldehyde 7 which could be transformed into the tricyclic aldehyde 8b in a repeated Vilsmeier reaction. Final cyclization was achieved with sodium ethanolate yielding the extremly unstable diazacyclo-penta[cd]phenalene derivative 9.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/jlac.1990199001119
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