An Odorless Preparative Method of Sulfides and Thiocarboxylic S-Esters Using 3-(Alkylthio)-1,2-benzisothiazole 1,1-Dioxide

Article abstract of DOI:10.1246/bcsj.56.949

It was found that sodium salt of 1,2-benzisothiazole-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide (3).Treatment of 3 with piperidine produces the corresponding alkanethiol in situ quantitatively and subsequent treatment with various electrophiles gives the corresponding sulfides and thiocarboxylic S-esters in good yields.