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  • Inorganic Chemistry  (12)
  • Organic Chemistry  (6)
  • Industrial Chemistry
  • 1990-1994  (18)
  • 1994  (18)
  • 1
    Electronic Resource
    Electronic Resource
    A Novel Approach to 2,2-Disubstituted 1,2-Dihydro-4-phenylquinolines (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 608-614 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 2-(1-phenylvinyl)aniline and 4-chloro-2-(1-phenylvinyl)aniline with acetophenone derivatives, 1-(naphthalen-1-yl)ethanone and 1-(furan-2-yl)ethanone in toluene at 110-115° with toluene-4-sulfonic acid as a catalyst leads in good-to-excellent yields to the 2,2-disubstituted 1,2-dihydro-4-phenyl-quinolines 1-18 (Scheme 1, Table). The structure of the new racemic 1,2-dihydroquinolines 1-18 is determined by NMR spectroscopy. A reaction mechanism proceeding via a 6π-electrocyclic rearrangement of 2-(1-phenylvinyl)anils 19 as the key step is proposed for the formation of these compounds (Scheme 1). The scope and limitations of the novel methods are discussed (Scheme 2).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770303
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  • 2
    Electronic Resource
    Electronic Resource
    2,3-Dihydrospiro[1H-4- and 5-azabenzimidazole-2,1′ -cyclohexane] ( = Spiro[cyclohexane-1,2′(3′H)-1′H-imidazo[4,5-b]pyridine] and Spiro[cyclohexane-1,2′(3′H)-1′H-imidazo[4, 5-c]pyridine]): Reactions with NucleophilesDedicated to Rolf Huisgen on the occasion of his 75th birthday (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 2175-2190 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The readily available title compounds 4a and 24 react with N-, O-, S-, and C-nucleophiles in presence of MnO2 to give the corresponding mono- or disubstituted 2H-azabenzimidazoles ( = azaisobenzimidazoles), e.g., 11-18 and 26a-h, respectively, or 2,3-dihydro-1H-azabenzimidazoles ( = dihydro-azabenzimidazoles) such as 9 and 10 and 27 and 28, respectively, by a 1, 4- or 1,6-Michael addition (Schemes 2 and 4). The bromo-dihydro-1H-azabenzimidazole 4b lost the Br-atom when treated with piperidine or morpholine yielding the corresponding disubstituted 2H-azabenzimidazole 21 (Scheme 3). Reductive ring opening of the substituted spiro compounds leads to mono- and disubstituted diaminopyridines which are intermediates for fused pyridine ring systems with substituents often not available by conventional routes and of potential pharmaceutical interest (see 32-37). E.g., starting from 4a, a three-step synthesis of the analgesic flupirtine maleate (= ethyl {2-amino-6-[(4-fluorobenzyl)amino]pyridin-3-yl}carbamate maleate = Katadolon®; 39) and of its non-fluorinated derivative D-7195 is described. Its analogue 40 was similarly made from the spiro compound 24.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770811
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  • 3
    Electronic Resource
    Electronic Resource
    Komplexierung von 1,4-Dihydro-1,4-diborafulvenen mit Ni(cod)- und Pt(cod)-FragmentenHerrn Professor Hubert Schmidbaur zum 60. Geburtstag gewidmet. (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 2393-2396 
    Details
    ISSN: 0009-2940
    Keywords: 1,4-Diborafulvenes, 1,4-dihydro- ; Slipped triple-decker ; Nickel complexes ; platinum complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Complexation of 1,4-Dihydro-1,4-diborafulvenes with Ni(cod) and Pt(cod) Fragments*Reactions of the 1,4-diborapentafulvene derivatives 1 and 2a, b with M(cod)2 (M = Ni, Pt) yield the complexes [(η5-1)Ni-(cod)] (8), [(μ,η2η5-2a){Ni(cod)}2] (9a), [(μ,η2,η5-2b){Ni(cod)}2] (9b), and [(μ,η2,η5-2a){Pt(cod)}2] (10). Compounds 9 and 10 are the first examples of complexes with 2a, b as a μ,η2,η5-ligand. The X-ray structure analyses of 9b and 10 are described.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941271209
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  • 4
    Electronic Resource
    Electronic Resource
    Ein neuer Zugang zu 1,2- und 1,3-DiborolHerrn Prof. Dr. Joachim Knappe zum 65. Geburtstag gewidmet. (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 1363-1368 
    Details
    ISSN: 0009-2940
    Keywords: 1,2-Diboroles, 2,5-dihydro- ; 1,3-Diboroles, 2,3-dihydro- ; Cobalt complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A New Approach to 1,2- and 1,3-DiboroleHerrn Prof. Dr. Joachim Knappe zum 65. Geburtstag gewidmet.Diaminoborylation of 1,3-dilithiopropenes leads to the (Z)-1,3-bis(diaminoboryl)propenes 4a, b, which are transformed by an amine/chlorine exchange to the (Z)-1,3-bis(aminochloroboryl)propenes 5a, b. These react with sodium to yield the 2,5-dihydro-1H-1,2-diboroles 2c, d, whereas the reaction with potassium leads to the 2,3-dihydro-1H-1,3-diboroles 6a, b by rearrangement of the C3B2 skeleton. The constitutions of the heterocycles 2c, d and 6a, b are established by X-ray structure analyses. Reaction of the 1,2-diboroles 2c, d with (C5H5)Co(C2H4)2 leads to the red (1-borabutadiene)cobalt complexes 3c, d. In 3c a sigmatropic rearrangement is studied by NMR spectroscopy.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270807
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  • 5
    Electronic Resource
    Electronic Resource
    Electronic Structure of Mono- and Bis(carbonyliron) as well as Bis(cyclopentadienyliron) Complexes of 1,4-Dihydro-1,4-diboranaphthalene (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 1557-1561 
    Details
    ISSN: 0009-2940
    Keywords: MO calculations, EH ; Iron, tricarbonyl(η6-1,4-dihydro-1,4-diboranaphthalene)- ; Bis(tricarbonyliron) ; Dicarbonyliron-tricarbonyliron ; Bis(cyclopentadienyliron) complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The structure and bonding of four iron complexes involving the 1,4-dihydro-1,4-diboranaphthalene ligand C8B2H8 (1), namely of the complexes (CO)3Fe(η6-C8B2H8) (2), (μ, η4,η6-C8B2H8)[Fe(CO)3]2 (3), (CO)3Fe(μ,η4,η6-C8B2H8)Fe(CO)2 (4), and of the triple-decker (μ,η6-C8B2H8)[Fe(η5-C5H5)]2 (5), have been investigated by means of the perturbational molecular orbital theory on the basis of the Extended Hückel calculations. Compounds 2 and 3 are 18-VE complexes, whereas 5 is a 30-VE species. The structure of 4 can be best described in terms of a 16-VE complex “Fe(CO)3 heterocycle” and a 18-VE “Fe(CO)2 carbocycle” unit with its iron centers being not directly bond.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270902
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  • 6
    Electronic Resource
    Electronic Resource
    Aminoglycoside Antibiotics  -  Modified, Enantiopure Sannamine- and Sporamine-Type Glycosyl Acceptors (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 1687-1697 
    Details
    ISSN: 0009-2940
    Keywords: Sannamines ; Sporamines ; Glycosyl acceptors, 4-epimers, fluorinated, enantiopure ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Along an established scheme, 1,2:3,4-dianhydrodeoxy-epi-inositol (3)  -  readily available from benzene  -  has been applied to expeditious syntheses of suitably protected, fluorinated, and epimerized aminoglycoside building blocks related to sannamine (rac-14a, rac-16a, rac-18a, rac-31a) and sporamine (rac-21a, rac-23a, rac-26a, rac-34a). By separation of diastereomers formed with (+)-(1-phenylethyl)amine (14c/ 14′c; 16c/16'c) or with (-)-camphanic acid (14e/14'e) and by enzymatic hydrolysis (rac-14b) access is gained to enantiopure glycosyl acceptors.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270920
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesen, Struktur und Eigenschaften von 1,2,5-PhosphadiborolanenHerrn Professor Otto J. Scherer zum 60. Geburtstag gewidmet. (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 329-331 
    Details
    ISSN: 0009-2940
    Keywords: 1,2,5-Phosphadiborolanes ; 1,2,5-Thiadiborolanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses, Structure and Properties of 1,2,5-PhosphadiborolanesReactions of (Z)-1,2-bis[chloro(diisopropylamino)boryl]ethane with Li2PC6H5 and of 1,2-bis[chloro(diisopropylamino)boryl]-1,2-diisopropylideneethane with [LiPh2·dme] yield the 1,2,5-phosphadiborolanes 1 and 2, respectively. The compounds are characterized by 1H-, 11B-, 13C-, and 31P-NMR spectroscopy as well as an X-ray structure analysis of 2. Low-temperature 1H-NMR studies show that the inversion barrier at P is distinctly lower than that of related unsaturated compounds. This might be the result of a favorable B—P-π interaction in the transition state of the inversion at the phosphorus atom. Reaction of 1 with S8 or CS2 leads to the 1,2,5-thiadiborolane 3.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270208
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  • 8
    Electronic Resource
    Electronic Resource
    Diastereoselective Functionalization of a Spherand-Type Calixarene (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 427-432 
    Details
    ISSN: 0009-2940
    Keywords: [1n]Metabiphenylophanes ; Calixarenes ; Spherands ; Diastereoselectivity ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Condensation of 5,5′-di-tert-butyl-2,2′-dihydroxybiphenyl (1) with formaldehyde yields a cyclic trimer 2 (and tetramer 3) having three (four) methylene groups less than a calix[6]-arene (calix[8]arene). Alkylation of the (flexible) trimer with ethyl bromoacetate gives exclusively the stereoisomer 4 with C2 symmetry, while the isomer with D3 symmetry is not observed. Two isomers 6a and 6b (C2 and C1 symmetry) are obtained by treatment with tert-butyl bromoacetate which both are converted by transesterification with methanol into the same hexamethyl ester 5 having C2 symmetry. These results are rationalized by restricted rotation around Ar—Ar bonds for larger O-alkyl groups also around Ar—CH2—Ar bonds. The structure of the hexaethyl ester 4 is also confirmed by single crystal X-ray analysis.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270219
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  • 9
    Electronic Resource
    Electronic Resource
    Synthese, Kristallstruktur und Reaktionen neuartiger metallacyclischer Dioxo- und Aminooxocarben-Komplexe des Eisens (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 711-715 
    Details
    ISSN: 0009-2940
    Keywords: Iron compounds ; Carbene complexes ; Metallacycles ; 2H-Pyrans ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis, Crystal Structure, and Reactions of Novel Metallacyclic Dioxo- and Aminooxocarbene Complexes of IronThe novel cationic iron carbene complexes 9 and 11 are readily prepared from the corresponding ferra lactones 7 and lactams 10, respectively. With nucleophiles the complexes 9 react chemoselectively either at the methyl group of the methoxy residue or at the terminal allylic C atom. In contrast to similar tungsten complexes 6, compounds 9 show “carbene activity” only when olefin and carbene ligands are separated by two atoms. Novel tricarboryl(2H-pyran)iron complexes 18 are obtained by a regioselective intramolecular carbene transfer in 9 once switched to the active form 17 by deprotonation using silyl enol ether 16 as a base.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270421
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  • 10
    Electronic Resource
    Electronic Resource
    J-Aggregate von 4-Iod-bis(dimethylamino)heptamethinium-triiodid Synthese, Struktur und optische EigenschaftenHerrn Professor Reinhard Schmutzler zum 60. Geburtstag gewidmet. (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 893-896 
    Details
    ISSN: 0009-2940
    Keywords: Iodination ; Streptopolymethine ; Cyanine dye aggregates ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: J-Aggregates of 4-Iodo-bis(dimethylamino)heptamethine Triiodide.  -  Synthesis, Structure, and Optical PropertiesIodination of heptamethincyanine 2a gives the title compound 3. Its cations display all-trans configuration in solution and in the crystalline state. In contrast to cations of 2a, those of 3 form one-dimensional J aggregates, as proved by X-ray analysis and optical reflection spectroscopy.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270517
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