Selective reductions. 30. Effect of cation and solvent on the reactivity of saline borohydrides for reduction of carboxylic esters. Improved procedures for the conversion …

HC Brown, S Narasimhan, YM Choi

Index: Brown, Herbert C.; Narasimhan, S.; Choi, Yong Moon Journal of Organic Chemistry, 1982 , vol. 47, # 24 p. 4702 - 4708

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Citation Number: 156

Abstract

A comparative study of the relative reactivity of saline borohydrides (Li, Na, Ca) for the reduction of carboxylic esters has been made in selected solvents (ether, tetrahydrofuran, diglyme, 2-propanol, and ethanol) at 25" C. In ether solvents the reactivity follows the trend LiBH4> Ca (BH4) 2> NaBH,. On the other hand, in alcohol solvents the order of reactivity is Ca (BH4) 2> LiBH,> NaBH4. The reactivities of LiBH4 in ethyl ether and THF, of Ca (BH,), ...