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

被引:115
作者
Billard, T [1 ]
Roques, N [1 ]
Langlois, BR [1 ]
机构
[1] Univ Lyon 1, CNRS, Lab Chim Organ 3, F-69622 Villeurbanne, France
关键词
D O I
10.1021/jo980649a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trifluorothioacetates (CF3CO-S-R, from (CF3CO)(2)O and thiols) as well as trifluoromethanethio-or trifluoromethaneselenosulfonates (CF3SO2-Y-R; Y = S, Se; from CF3SO2Na, RYYR, and Br-2) can be formally decarbonylated or desulfonylated, respectively, provided that they are photolyzed at 40 degrees 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.
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页码:3813 / 3820
页数:8
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