Acyl azide photolysis. Proximity and ring-size factors and mechanism
Open Access
- 1 November 1967
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 45 (21) , 2599-2604
- https://doi.org/10.1139/v67-422
Abstract
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. The importance of proximity in determining the γ- to δ-lactam ratio is emphasized.Keywords
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