Thioalkoxytributyl- and Thioalkoxytriphenylphosphonium Salts : Preparation and Application to the Synthesis of Thiolesters and Unsymmetrical Sulfides(Organic,Chemical)

概要

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Thioalkoxyphosphonium salts, Ph_3P^+SR ClO_4^-(3) and Bu_3P^+SR X^- (X= ClO_4 and BF_4)(5), have been prepared from the corresponding tertiary phosphines and disulfides by simple procedures, which involve (i) constant current electrolysis in acetonitrile in the presence of either HClO_4 (for 3) or PhCOOH and LiX (for 5), and (ii) stirring an equimolar mixture of a phosphine, a disulfide, PhCOOH, and LiX in acetonitrile at ambient temperature. For the preparation of 3, which have been reported as useful reagents for the synthesis of unsymmetrical disulfides, the electrochemical method is recommended, while for 5 the latter non-electrochemical procedure gave better results. Reactions of the phosphonium salts 5 with carboxylic acids and primary alcohols in benzene at ambient temperature gave thiolesters and unsymmetrical sulfides, respectively, in fair to excellent yields.
公益社団法人日本薬学会の論文
1987-11-25