Hydrocyanation of some α,β-unsaturated ketones, and the synthesis of some unusual isoxazoles

Abstract

β-Cyano-α-methylcycloalkanones are regiospecifically nitrosated at the α-position by pentyl nitrite in methanolic sodium methoxide to give fused isoxazolo-lactams via a pathway probably involving sequential cycloalkanone cleavage, isoxazole formation and lactamisation. The chemistry of some new compounds derived from the hydrocyanation products of (–)-carvone is described.