SYNTHESIS OF GAMMA-UNSATURATED ENAMIDES BY N-ACYLATION OF IMINES DERIVED FROM GAMMA-UNSATURATED AMINES

N-Formyl-N-styryl amines (1-3) were prepared from imines derived from gamma-unsaturated amines and phenylacetaldehyde by formylation with et hyl formate in the presence of sodium methoxide. Formation of the corr esponding N-acetyl analogues was less selective, as was demonstrated b y reaction of 2-(cyclohexen-1-yl)ethyl]-2-(phenyl)ethylidenimine and a cetyl chloride. Some N-acetyl-N-vinyl amines (7, 11) were prepared fro m the corresponding imines by acetylation with acetyl chloride or acet ic anhydride. N-Formyl-N-vinyl amines (12, 13) were synthesized from t he appropriate imines using acetic formic anhydride as formylating age nt.