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Photochemisch induzierte Reaktionen von 3-Amino-2H-azirinen


Dietliker, Kurt; Heimgartner, Heinz (1983). Photochemisch induzierte Reaktionen von 3-Amino-2H-azirinen. Helvetica Chimica Acta, 66:262-295.

Abstract

Photochemically Induced Reactions of 3-Amino-2H-azirines. Irradiation of 3-(N-methylanilino)-2H-azirines with a mercury low pressure lamp induces the cleavage of the C(2),C (3)-ring bond thus affording nitrilio- methanide dipols, substituted by an amino group at C(1). Depending on the substitution pattern at C(3), these intermediates can be trapped by dipolarophiles to yield five-membered heterocycles with high regioselectivity, or they undergo a 1,4-H-shift forming 2-azabutadiene derivatives. Further, the dipol is protonated at C (1) even by weak CH-acids.

Abstract

Photochemically Induced Reactions of 3-Amino-2H-azirines. Irradiation of 3-(N-methylanilino)-2H-azirines with a mercury low pressure lamp induces the cleavage of the C(2),C (3)-ring bond thus affording nitrilio- methanide dipols, substituted by an amino group at C(1). Depending on the substitution pattern at C(3), these intermediates can be trapped by dipolarophiles to yield five-membered heterocycles with high regioselectivity, or they undergo a 1,4-H-shift forming 2-azabutadiene derivatives. Further, the dipol is protonated at C (1) even by weak CH-acids.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1983
Deposited On:08 Jul 2014 10:32
Last Modified:05 Apr 2016 17:57
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung

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