Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides

Citation
T. Billard et al., Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides, J ORG CHEM, 64(11), 1999, pp. 3813-3820
Citations number
65
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
11
Year of publication
1999
Pages
3813 - 3820
Database
ISI
SICI code
0022-3263(19990528)64:11<3813:SUOTAS>2.0.ZU;2-R
Abstract
Trifluorothioacetates (CF3CO-S-R, from (CF3CO)(2)O and thiols) as well as t rifluoromethanethio-or trifluoromethaneselenosulfonates (CF3SO2-Y-R; Y = S, Se; from CF3SO2Na, RYYR, and Br-2) can be formally decarbonylated or desul fonylated, respectively, provided that they are photolyzed at 40 degrees C in the presence of 1 equiv of the corresponding disulfide or diselenide. Tr ifluoromethyl sulfides or selenides are obtained, and the added disulfide ( or diselenide) is recovered after reaction. In such a way, S-(trifluorometh yl)cysteine derivatives can be obtained.