Acyl azide photolysis. Proximity and ring-size factors and mechanism
1967 ◽
Vol 45
(21)
◽
pp. 2599-2604
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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.
1967 ◽
Vol 32
(6)
◽
pp. 2122-2133
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Keyword(s):
Keyword(s):