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

Article abstract of DOI:10.1021/ja00533a024

Preparative and mechanistic details are described for the conversion of selenides into hydrocarbons RH> by heating with triphenyltin hydride at about 120 deg C.The process has been extended to selenoacetals in a form that constitutes a reduction methods for carbonyl compounds 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 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 as the corresponding dichlorides , are reduced under very mild conditions (25-80 deg 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.