A simple synthetic route to 4-methylcamphor: mechanistic aspects

Abstract

A mechanism proposed for the rearrangement of (+)-2-methylenebornane (8) to a mixture of (+)-4-methylisobornyl acetate (5) and its enantiomer (ent-5) is supported by evidence obtained by investigating the rearrangement of deuterated 2-methylenebornane. Keywords: 4-methylcamphor, Wagner–Meerwein rearrangement, 6,2-hydride shift, 9-bromo-4-bromomethylcamphor.