The Journal of Organic Chemistry

Synthesis of (racemization prone) optically active thiols by SN2 substitution using cesium thiocarboxylates

B Strijtveen, RM Kellogg

Index: Strijtveen, Bert; Kellogg, Richard M. Journal of Organic Chemistry, 1986 , vol. 51, # 19 p. 3664 - 3671

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Citation Number: 114

Abstract

The cesium salt of thioacetic acid is prepared by treatment with cesium carbonate. This salt has a solubility of about 0.7 M in DMF (even higher in Me, SO) at 50" C. The mesylates of (R)- 2-octanol, the ethyl ester and N, N-dimethyl amide of (&mandelic acid,(5')-ethyl lactate,(&methyl 3-phenyllactate, and@)-diethyl malate underwent clean SN2 substitution in DMF solution. Racemization occurred only in the case of the mesylate of ethyl mandelate ...

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