The Formation of cis-and trans-Perhydrobenzofurans from 2-(2-Methoxycyclohexyl) ethanol Derivatives. Reactions Proceeding through Methoxyl Participation

SE Cantor, DS Tarbell

Index: Cantor,S.E.; Tarbell,D.S. Journal of the American Chemical Society, 1964 , vol. 86, p. 2902 - 2909

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Citation Number: 14

Abstract

cis-and Irans-(2-methoxycyclohexylethanol and homologs have been synthesized and are shown to form cis-and trans-perhydrobenzofurans when treated with tosyl chloride-pyridine. An oxygen-18 labeling study has shown that the methoxyl oxygen is retained during the cyclization; the hydroxyl oxygen is the one eliminated. The cyclization is believed to involve a cyclic oxonium ion intermediate; this is supported by the isolation of chloro compounds, ...