Kinetics of the dienone–phenol rearrangement and basicity studies of some cyclohexa-2,5-dienones

Abstract

The basicities have been measured of 5,6,7,8-tetrahydro-4a-methylnaphthalen-2(4aH)-one,5,6,7,8-tertrahydro-45,6,7,8-tetrahydro-4a,8-dimethylnaphthalen-2(4aH)-one, androsta-1,4-diene-3,17-dione, 2,4,4-trimethylcyclohexa-2,5-dienone, and 2,4,4,6-tetramethylcyclohexa-2,5-dienone. The kinetics and products of the dienone–phenol rearrangements of these dienones in aqueous sulphuric and perchloric acids at 25 °C have been studied; limited kinetic studies have also been made in aqueous sulphuric acid at 40 °C. The effects of substitution pattern on the basicities and rates of rearrangement are discussed.