Reductions with Metal Hydrides. XV. Reduction of 2-Tetrahydropyranyl and 2-Tetrahydrofuranyl Thioethers with Lithium Aluminum Hydride-Aluminum Chloride

EL Eliel, BE Nowak, RA Daignault

Index: Eliel,E.L. et al. Journal of Organic Chemistry, 1965 , vol. 30, p. 2448 - 2450

Full Text: HTML

Citation Number: 13

Abstract

We have now applied this reduction to 2-tetrahydropryanyl and 2-tetrahydrofuranyl thioethers which are readily synthesized by the addition of mercaptans to. 2, 3-dihydropyran and 2, 3-dihydrofuran1 respectively, and which, being monothioacetals, are subject to the cleavage reaction by “mixed hydride.” Unlike the oxygen analogs described in the preceding paper, 4 the sulfur compounds underwent selective cleavage of the ring carbon-oxygen ...