The Oxidation of Various Acyclic Monoterpene Hydrocarbons in Polar Aprotic Solvents

Abstract

Autoxidation of alloocimene [1], myrcene [2], and dihydromyrcene [3] in polar aprotic solvents was carried out. In dimethyl sulfoxide (DMSO) or N, N-dimethylformamide (DMF), the oxidation of [1] gave predominantly 5-isopropyl-2-methyl-2, 4-cyclohexadien-1-ol [10] and 2-isopropyl-5-methyl-2, 4-cyclohexadien-1-ol [13]. In DMSO, the oxidation of [2] gave 2, 6-dimethyl-7-octen-3-one [19]. In DMF, [2] gave linalool [6] whereas [3] gave 6, 7-epoxy-3, 7-dimethyl-1-octene [18] as major products with high conversion ratio and selectivity.