Synthesis of 3-substituted trans-2-oxadecalins and 1-substituted trans-2-oxahydrindanes

A study was carried out of the intramolecular cyclization of trans-1-methoxymethyl-2-(1-hydroxyalkyl)cyclohexanes and trans-1-methoxymethyl-2-(2-hydroxyalkyl)cyclohexanes by the action of acid chlorides of phosphorous, sulfurous and p-toluenesulfonic acids with the formation of 1-substituted trans-2-oxahydrindanes in low yields and 3-substituted trans-2-oxadecalins in high yields. A relationship has been established between the yields of the cyclization products and the nature of the halogenating agent. The cyclization does not proceed via an intermediate oxonium ion, but by means of an intermolecular electronic transition.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1865–1877, August, 1991.