Rearrangement of ketones. Part 3. Kinetic study and intermediate complexes in the reaction of t-butyl phenyl ketone with aluminium chloride

Abstract

A kinetic study of the rearrangement of t-butyl phenyl ketone to 3-methyl-3-phenylbutan-2-one with aluminium chloride is reported. In addition, a study by ¹H and ¹³C n.m.r. of the system t-butyl phenyl ketone–aluminium chloride in benzene shows the consecutive formation of a 1:1 complex and a later complex species, which according to the kinetic scheme proposed may have 2:5 stoicheiometry. This is the reactive intermediate in the rearrangement process.