1,3-Dipolar cycloaddition reactions of aziridines onto 1,2,3-triphenylcyclopropene

Abstract

1,3-Dipolar cycloaddition reactions of 1-cyclohexyl- and 1-methyl-2-aroyl-3-phenylaziridines (2)–(7) with 1,2,3-triphenylcyclopropene(1) gave 3-cyclohexyl-and 3-methyl-2-aroyl-1,4,5,6-tetraphenyl-3-azabicyclo[3.1.0]-hexanes (8)–(13), respectively, the configurations of which were assigned as (14) based upon comparisons of the ¹H n.m.r. spectrum of the 1 : 1 adduct (8) with that of its stereoisomer (8′). On treatment of the 3-azabicyclo-[3.1.0]hexanes (8) and (13) with tetrachloro-o-benzoquinone, 2-benzoyl-3,4,5,6-tetraphenylpyridine (20) was obtained.