PHOTO-ADDITION OF <i>N</i>-NITROSODIALKYLAMINES TO CYCLOHEXENE

Abstract

Under the simultaneous influence of light and an acid, the nitrosamines derived from four heterocyclic amines readily form 1:1 photo-adducts with cyclohexene giving excellent yields of 2-tert-aminocyclohexanone oximes. While N-nitrosodi-n-butylamine, under similar conditions, gives a fair yield of the 1:1 photo-adduct, N-nitrosodicyclohexylamine and N-nitrosodiisopropylamine do not. The conformations of these oximes are discussed in conjunction with the n.m.r. data.