Oxidation of 3-carene by lead tetraacetate in acetic acid

Abstract

1. The oxidation of 3-carene with P (OAc)4 in acetic acid was studied. The following were found in the reaction products: m-methylisopropenylbenzene; 3,6,6-trimethylcycloheptadiene-2,4-one-1; 3-acetyl-6,6-dimethylbicyclo-[3,1,0]-hexane; the acetate of carene-4(7)-ol-3; an acetate with the presumed structure of the acetate of p-menthadiene-1,8(9)-ol-5; the acetate of 2-m-tolylpropanol-2; the acetate of trans-2,4-caranediol. 2. During the reaction there are rearrangements of the carene structure to p- and m-menthadiene, bicyclo-[3,1,0]-hexane, and cycloheptadiene systems. 3. The difference in the course of the oxidation of 3-carene with Pb(OAc)4 in acetic acid and in benzene was obtained by the influence of temperature and solvent. © 1970 Consultants Bureau.