Photolysis of hexanoyl azide in cyclohexane gave 6-methyl-2-piperidone (13%), 5-ethyl-2- pyrrolidone (8%), and N-cyclohexylhexanamide (3%). In contrast, photosensitized decomposition of the azide with acetophenone gave hexanamide (78%), cyclohexene (11%), and dicyclohexyl (11%), but no lactams. It is concluded that the direct photolysis gives singlet acyl nitrene as the reactive species, which yields the δ-lactam preferentially. ...
