The Journal of Organic Chemistry

Preparation of chiral 1-deuterio benzenemethanethiols by using. alpha.,. beta.-elimination of carbanions derived from benzylic thioethers

JF Biellmann, H D'Orchymont

Index: Biellmann, Jean-Francois; d'Orchymont, Hugues Journal of Organic Chemistry, 1982 ,  vol. 47,  # 15  p. 2882 - 2886

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Citation Number: 9

Abstract

The a',,!? elimination of the carbanion derived from [a-2H2] benzyl isolongifolyl thioether and [a-2H2] benzyl camphyl thioether gives the chiral [~-~ H] benzyl mercaptan, the S isomer with 38 f 6% ee and the R isomer with 49 f 7% ee. The chirality of the [a-2H] benzyl mercaptan was determined by optical rotation of [a-2H] benzyl methyl thioether and thiosulfone. The enantiomeric excess was evaluated from 'H NMR measurement of ethyl ( ...