The reaction of sodium 1,3-diphenyl-2-azapropenide with 1,2-epoxycyclohexane

Abstract

Ring opening of 1,2-epoxycyclohexane by the title aza-allylic anion afforded a mixture of anions, the quenching and subsequent hydrolysis of which gave rise to trans-2-(α-aminobenzyl)cyclohexanol (10) and benzylamine as the basic fraction, and to either 1-benzoylcyclohexene (11) or trans-2-benzoylcyclohexanol (12), cis-2-benzoylcyclohexanol (14), and benzaldehyde as the neutral fraction: the type of ketone obtained depended upon the hydrolytic conditions. The perhydrobenzoxazine (7) was shown to be the precursor of compound (10). Sodium 1,3-diphenyl-2-azapropenide thus behaved both as an α-benzylamine carbanion equivalent and as a benzoyl anion equivalent.