Tributyltin hydride: a selective reducing agent for 1, 3-dithiolanes

…, RA Stringham, T Nitasaka, KG Glasscock

Index: Gutierrez, Carlos G.; Stringham, Rex A.; Nitasaka, Tadashi; Glasscock, Karl G. Journal of Organic Chemistry, 1980 , vol. 45, # 17 p. 3393 - 3395

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Citation Number: 70

Abstract

Tri-n-butyltin hydride has been found to be an effective and selective agent for complete or partial desulfurization of 1, 3-dithiolanes 1. The reaction of 1 with 4 equiv of tri-n-butyltin hydride in the presence of 2, 2'-azobis-(isobutyronitrile) results in complete desulfurization, giving hydrocarbons 2 in good yield, ethane, and bis (trin-butyltin) sulfide. Two equivalents of hydride specifically cleave the two geminal CS bonds in 1 to give hydrocarbons 2 and ...