Synthetic Uses of Thio- and Selenoesters of Trifluoromethylated Acids. 1. Preparation of Trifluoromethyl Sulfides and Selenides

Article abstract of DOI:10.1021/jo980649a

Trifluorothioacetates (CF₃CO-S-R, from (CF₃CO)₂O and thiols) as well as trifluoromethanethio-or trifluoromethaneselenosulfonates (CF₃SO₂-Y-R; Y = S, Se; from CF₃SO₂Na, RYYR, and Br₂) can be formally decarbonylated or desulfonylated, respectively, provided that they are photolyzed at 40°C in the presence of 1 equiv of the corresponding disulfide or diselenide. Trifluoromethyl sulfides or selenides are obtained, and the added disulfide (or diselenide) is recovered after reaction. In such a way, S-(trifluoromethyl)cysteine derivatives can be obtained.