Sulfinic Acids and Related Compounds. 18. Synthesis and Properties of Derivatives of 2-Mercaptoethanesulfinic Acid

Article abstract of DOI:10.1021/jo00376a035

Use of thiirane 1,1-dioxide (2) affords a useful synthesis of ethanesulfinates with the following functions in the 2-position: thiol, disulfide, trisulfide, thiosulfate, thiosulfonate, and phosphorothioate.The sulfinic esters generally were rather stable, but in several instances the salts gave unexpected results because of involvement of the sulfinate function with the sulfur atom of the 2-substituent; for example, the thiosulfonate p-MeC6H4SO2(CH2)2SO2Na (17) in water quickly liberated sodium p-toluenesulfinate (15) and gave an insoluble polymer shown by mass spectra to have the structure p-MeC6H4SO2nSO2Na (26).Aryl disulfides of the structure ArSS(CH2)2S(O)OMe were reasonably stable thermally but were quite sensitive to light.