Organic Tellurium and Selenium Chemistry. Reduction of Tellurides, Selenides, and Selenoacetals with Triphenyltin Hydride

Abstract

Preparative and mechanistic details are described for the conversion of selenides into hydrocarbons [RSePh → RH] by heating with triphenyltin hydride at about 120 °C. The process has been extended to selenoacetals in a form that constitutes a reduction method for carbonyl compounds [RR'C=0 → RR'C(SePh)2 → RR'CH2], Selective reduction of selenoacetals in the presence of thioacetals is possible. Cold-labeled species can be prepared by using triphenyltin deuteride. Tellurides [RTePh] are available easily without problems arising from exposure to air provided that the work is done in a photographic darkroom equipped with a red safety light. These tellurides, as well asthe corresponding dichlorides [RTe(Cl2)Ph], are reduced under very mild conditions (25-80 °C) by triphenyltin hydride. The selenium- and tellurium-based chemistry has been used for the unusual process of reducing an epoxide in the presence of a ketone carbonyl. © 1980, American Chemical Society. All rights reserved.