S-trifluoromethyl esters of thiocarboxylic acids, RC(O)SCF3

被引:27
作者
Kremlev, MM
Tyrra, W
Naumann, D
Yagupolskii, YL
机构
[1] Univ Cologne, Inst Anorgan Chem, D-50939 Cologne, Germany
[2] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02094 Kiev, Ukraine
关键词
S-trifluoromethyl esters; acid chlorides; halide substitution;
D O I
10.1016/j.tetlet.2004.06.073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
S-Trifluoromethyl esters of different types of thiocarboxylic acids have been prepared in moderate to excellent yields from halide Substitution reactions of the corresponding acid chlorides and tetramethylammonium trifluoromethylthiolate. C6F5C(O)SCF3 undergoes a surprising rearrangement on attempted isolation to give 4-CF3SC6F4C(O)F, which was converted into the corresponding acid. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6101 / 6104
页数:4
相关论文
共 10 条
[1]   A xanthate transfer radical process for the introduction of the trifluoromethyl group [J].
Bertrand, F ;
Pevere, V ;
Quiclet-Sire, B ;
Zard, SZ .
ORGANIC LETTERS, 2001, 3 (07) :1069-1071
[2]   PREPARATION AND PROPERTIES OF (TRIFLUOROMETHYLTHIO)-SUBSTITUTED CARBONYL-COMPOUNDS [J].
HAAS, A ;
LIEB, M .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (08) :2891-2894
[3]   Perfluoroorganochalcogenyl-ketenes -: IV.: Bis(perfluoroorganochalcogenyl)ketenes (RfE)2C=C=O (Rf = CF3, C6F5, E = S, Se):: synthons with a high preparative potential [J].
Haas, A ;
Radau, G .
JOURNAL OF FLUORINE CHEMISTRY, 1998, 89 (01) :9-18
[4]   SYNTHESIS AND PROPERTIES OF BIS-(TRIFLUOROMETHYLTHIO)-MERCURY [J].
MAN, EH ;
COFFMAN, DD ;
MUETTERTIES, EL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (14) :3575-3577
[5]   Reactions of trifluoromethylthiocopper with halomethanes [J].
Munavalli, S ;
Rossman, DI ;
Rohrbaugh, DK ;
Ferguson, CP ;
Durst, HD .
JOURNAL OF FLUORINE CHEMISTRY, 1996, 76 (01) :7-13
[6]   SIMULTANEOUS SCISSION OF C-S AND S-S BONDS OF BIS(TRIFLUOROMETHYL)TRISULFIDE BY GRIGNARD-REAGENTS [J].
MUNAVALLI, S ;
ROSSMAN, DI ;
ROHRBAUGH, DK ;
FERGUSON, CP ;
SZAFRANIEC, LJ .
JOURNAL OF FLUORINE CHEMISTRY, 1992, 59 (01) :91-99
[7]   A new synthesis of trifluoromethanethiolates - characterization and properties of tetramethylammonium, cesium and di(benzo-15-crown-5)cesium trifluoromethanethiolates [J].
Tyrra, W ;
Naumann, D ;
Hoge, B ;
Yagupolskii, YL .
JOURNAL OF FLUORINE CHEMISTRY, 2003, 119 (01) :101-107
[8]  
TYRRA W, UNPUB
[9]  
Wessel W, 2001, Z ANORG ALLG CHEM, V627, P1264, DOI 10.1002/1521-3749(200106)627:6<1264::AID-ZAAC1264>3.0.CO
[10]  
2-J