Journal of the American Chemical Society

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

SE Cantor, DS Tarbell

文献索引：Cantor; Tarbell Journal of the American Chemical Society, 1964 , vol. 86, p. 2902,2907

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被引用次数: 14

摘要

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, ...