Reaction of benzoyl(phenyl)acetaldehyde with N-phenylhydroxylamine: a re-examination

Abstract

N-(2-Benzoylstyryl)-N-phenylhydroxylamine (3), the primary condensation product between benzoyl(phenyl)-acetaldehyde (1) and N-phenylhydroxylamine (2) has been isolated, and its tautomerism studied. This compound readily dehydrates to C-benzoyl-CN-diphenylketen imine (5) which, in turn, gives the final products by addition, respectively, of water [benzoyl(phenyl)acetanilide (12)], acetic acid [acetylated benzoyl(phenyl)acetanilide (7)], N-phenylhydroxylamine [2-phenylimino-3,4,5-triphenyloxazoline (10)], or benzoylphenylacetaldehyde [2-benzoylstyryl [N-phenyl(benzoyl)phenylacetimidate or tautomer (9), produced].