THE CLEAVAGE OF CARYOPHYLLENE OXIDE CATALYZED BY TETRACYANOETHYLENE

The cleavage of caryophyllene oxide under novel, mild and clean condit ions, using tetracyanoethylene as a catalyst, is described. Alcoholysi s leads to clovenol-2-ether derivatives as major products. When dipola r aprotic solvents were used, rearrangement products were not formed a nd compounds from elimination reaction were obtained. The ratio of cyc lization to elimination products reflects the extent to which the part ially delocalized carbocation may be stabilized by the nucleophilic so lvent. Copyright (C) 1996 Elsevier Science Ltd