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Photochemically Induced 1,3-Dipolar Cycloadditions of 3-Amino-2H-azirines


Dietliker, Kurt; Stegmann, werner; Heimgartner, Heinz (1980). Photochemically Induced 1,3-Dipolar Cycloadditions of 3-Amino-2H-azirines. Heterocycles, 14(7):929-934.

Abstract

Irradiation of 3-(N-methylanilino)-2H-azirines in dimethoxyethane solution in the presence of dipolarophiles leads to five-membered heterocycles in 40-60% yield. A reaction mechanism via splitting of the C(2),C(3)-bond and formation of a nitrilio methanide which then undergoes a thermal 1,3-dipolar cycloaddition is reasonable.

Abstract

Irradiation of 3-(N-methylanilino)-2H-azirines in dimethoxyethane solution in the presence of dipolarophiles leads to five-membered heterocycles in 40-60% yield. A reaction mechanism via splitting of the C(2),C(3)-bond and formation of a nitrilio methanide which then undergoes a thermal 1,3-dipolar cycloaddition is reasonable.

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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:English
Date:1980
Deposited On:29 Jul 2014 11:02
Last Modified:05 Apr 2016 17:59
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation

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