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Communication | Regular issue | Vol 14, No. 7, 1980, pp.929-934
Published online, 1st January, 1970
DOI: 10.3987/R-1980-07-0929
Photochemically Induced 1,3-Dipolar Cycloadditions of 3-Amino-2H-azirines

Kurt Dietliker, Werner Stegmann, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

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.