NOVEL PHOTOCHEMICAL HYDROLYSIS OF O-ACETYLPHENYLACETONITRILES TO AMIDES

Irradiation of o-acetylphenylacetonitriles 1a,b in methanol (lambda > 280 nm) leads to essentially quantitative photohydrolysis with formati on of the corresponding ketal amides 3a,b. The mechanism proposed for this novel reaction is supported by the qualitatively different photoc hemical behavior of 1c and by a labeling experiment with 1a-L that con firms transfer of the carbonyl oxygen atom of 1a to the amide oxygen a tom of 3a.