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  • 1
    Electronic Resource
    Electronic Resource
    Zur Reaktion von Halogen(trimethylsilyl)benzolen mit Elektrophilen und Basen - Carbodesilylierung und Eliminierung als Konkurrenzreaktionen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2113-2118 
    Details
    ISSN: 0009-2940
    Keywords: Halo(trimethylsilyl)benzenes, carbodesilylation and elimination of ; Carbodesilylation ; Elimination ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of Halo(trimethylsilyl)benzenes with Electrophiles and Bases - Carbodestlylation and Elimination as Competitive ReactionsElimination to dehydrobenzenes takes place as competitive reaction in the base-catalyzed carbodesilylation of 1-halo-2-(trimethylsilyl)benzenes 1 with carbonyl compounds 2 in the presence of furans 3, 6. Elimination is preferred with increasing leaving tendency of the halides (I 〉 Br 〉 〉 Cl 〉 〉 F) and with decreasing reactivity of the carbonyl compounds. Exclusive elimination to 1,2-didehydrobenzenes - which are trapped with furans - occurs in the reaction when no electrophiles are present.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240938
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  • 2
    Electronic Resource
    Electronic Resource
    Darstellung von Didehydropyridinen aus (Trimethylsilyl)pyridinen (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 2119-2125 
    Details
    ISSN: 0009-2940
    Keywords: Didehydropyridines, synthesis of ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preparation of Didehydropyridines from (Trimethylsilyl)pyridinesHalogen-substituted (trimethylsilyl)pyridines 2, 3, 5 - 7 and trifluoromethylsulfonyloxy-substituted (trimethylsilyl)pyridines 9b, 11b are obtained from 2- and 3-halopyridines 1, 4 or hydroxypyridines 8, 10, and 12. Reactions of the 3- and 2-(trimethylsilyl)pyridines 2,9b and 11b with bases in the presence of furans 15 give only protodesilylation or hydrolysis products but no indication is found for the formation of a 2,3-didehydropyridine. 3-Bromo-4-(trimethylsilyl)pyridine (5a) reacts with KOCMe3 in the presence of furan (15a) to give a mixture of products from which the isoquinoline derivative 20 and the tert-butoxypyridines 23, 24 are formed by addition to 3,4-didehydropyridine. Under comparable conditions far higher yields of 3,4-didehydropyridines are obtained by treatment of the 3-halo-2,4-bis(trimethylsilyl)pyridines 7 with strong bases.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240939
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    Paper (German National Licenses)
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