Disparate behavior of ketones and thioketones on reaction with organolithiums

KB Wiberg, AL Bartelson, WF Bailey

Index: Wiberg, Kenneth B.; Bartelson, Ashley L.; Bailey, William F. Tetrahedron Letters, 2011 , vol. 52, # 17 p. 2169 - 2171

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Citation Number: 4

Abstract

The reactions of alkyllithiums with ketones and thioketones proceed in fundamentally different ways. Whereas alkyllithiums add to the carbonyl carbon of ketones to give tertiary alcohols, the reaction with thioketones proceeds to give secondary thiols by reduction of the CS group. Transition states for the addition and reduction reactions of acetone and thioacetone in ethereal solution have been located and the computed activation free ...