Selective reductions. 29. A simple technique to achieve an enhanced rate of reduction of representative organic compounds by borane-dimethyl sulfide

HC Brown, YM Choi, S Narasimhan

Index: Brown, Herbert C.; Moon Choi, Yong; Narasimhan, S. Journal of Organic Chemistry, 1982 , vol. 47, # 16 p. 3153 - 3163

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Citation Number: 185

Abstract

A dramatic increase in the rate of reduction of esters by borane-dimethyl sulfide (BMS) is observed when dimethyl sulfide is removed from the reaction mixture. On the basis of this observation, a new, improved procedure has been developed for the reduction by BMS of respresentative organic functional groups, such as esters, nitriles, and amides. The procedure involves addition of BMS to the substrate in refluxing tetrahydrofuran, allowing ...