Electrophilic cyclization of α-series monoterpene ω-derivatives

New information is discussed concerning the protic and Lewis acid-initiated electrophilic cyclization reaction of -monoterpenols and their acetates; the distinguishing feature of these reactions is their termination by isopropenyl residues in these molecules. The reactions have been found to be general in nature, given additional functionalization of the terminator by chloro-, sulfonyl, sulfonylmethyl, or ester substituents. Cyclization of these linear substrates has also been shown to provide a convenient method for the synthesis of dimethylvinylcyclohexene derivatives and related cyclohexanediols, which are not readily available by other methods.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1361–1367, June, 1990.