Chemoselective reaction of a sulfonate ester with methoxide ions in preference to benzyl mercaptide anions

Abstract

1This paper is dedicated lo Professor Douglas E. Rya11 on the occasion of his 651h birthday RICHARD FRANCIS LANGLER and NANCY ANN MORRISON. Can. J. Chem. 65, 2385 (1987).

Sulfonyl esters 1: The reduction of tribromophenyl sulfonates with mercaptide anions

“…Reaction ofmercaptans with 2,4,6-tribromophenyl methanesulfonate 1 The conversion of benzenethiol into diphenyl disulfide will be used to illustrate the procedure that furnished the results in Table 1.…”

“…Methyl methanesulfonate is an intermediate in this reaction (1). Subsequently, a study of sulfonate esters as reagents for the one-pot condensation of mercaptans and alcohols to furnish sulfone precursors was initiated.…”

Synthesis and reactivity of fluorine-containing thiols and thioacyl halides

“…R F = CF 3 (15), H(CF 2 ) 2 (16), H(CF 2 ) 4 (17) The reactions were also carried out while heating the reaction mixture to 150 °C and then raising the tempera ture to 180 °C to complete the process, with simultaneous removal of the product. The resulting thioacyl chlorides 15-17 (≥95% purity) can be used without additional pu rification for subsequent transformations.…”