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

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.