chem.R ~ V ieob, . 84. 17-30
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Synthesis and Reduction of Thiocarboxylic 0-Esters BRIAN A. JONES
and JERAU) S. BRADSHAW’ ShrdkJ. 7 Er@harnYoung unlvenlly.Fmw, MPh 84602
Dspattment of Chmkby and Um InStlMs of -1
Rscehgd nprll 15. 1983 (Revised Manuscr@tRscehgd Augurt 4. 1983)
Contents 1. Introduction 11.
Reparatbn of Thiocarboxylic O-Esters A. Sulfhydrdysis of lmlno Esters B. Sulfhydrdysis of Dialltoxycerbonium Ions
Alcoholysis of Thloacyl Halides Addition of Alcohols to Thioketenes Direct SulMzation of Esters miolo-mion0 Rearrangements TransesterMcatbn of Thiocarboxylic O-€sters and Dilhlo Esters H. Reactions on Thiocarboxylic O-Esters I. Miscellaneous 111. Reductions of Thiocarboxyllc O-Esters I V . References
C. D. E. F. G.
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19 20 20 21 23 23 23 23
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I . Intmductlon Thiocarboxylic@esters are a elass of compounds that have received relatively little attention in the chemical literature. Recent efforts, however, have led to an increasing variety of synthetic methods for preparing these compounds as well as new applicationa for their use,both as synthetic intermediates and f i products. A recent review by Scheithauer and Meyer’ thoroughly describes the advances in this field through 1976. This review will follow a similar format hut will be much more narrow in scope. It will concern itself only with compounds bearing the functionality
