Photochemistry of 4-acyloxy-2-azabuta-1,3-dienes. A novel photochemical 1,2-acyl migration in an enol ester. The synthesis of 2,5-dihydro-oxazole derivatives
“…The formation of products (14) and (15) could arise by a variety of paths which are difficult to differentiate using only azaenone (7) because of the identical substitution at each end of the enone system. This problem can be surmounted using azaenone (8) which on irradiation is converted into analogous products (16) and (17). The identity of these products was established by the normal spectroscopic methods and also by comparison with photo products (14) and (15).…”
Section: Resultsmentioning
confidence: 99%
“…Hydrolysis of (16). Hydrolysis of keto imine (16) (10 mg, 0.019 mmol) afforded an oil which was identified as 0dibenzo ylbenzene.…”
Section: General Procedures For Irradiation Of Enonesmentioning
“…The formation of products (14) and (15) could arise by a variety of paths which are difficult to differentiate using only azaenone (7) because of the identical substitution at each end of the enone system. This problem can be surmounted using azaenone (8) which on irradiation is converted into analogous products (16) and (17). The identity of these products was established by the normal spectroscopic methods and also by comparison with photo products (14) and (15).…”
Section: Resultsmentioning
confidence: 99%
“…Hydrolysis of (16). Hydrolysis of keto imine (16) (10 mg, 0.019 mmol) afforded an oil which was identified as 0dibenzo ylbenzene.…”
Section: General Procedures For Irradiation Of Enonesmentioning
The acyloxy‐azabutadienes (I), on irradiation, undergo rearrangement by 1,2‐migration of the acyl group to yield the 2,5‐dihydro‐oxazoles (II), which are found to be the sole products of this photoreaction.
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