BIS(TRIFLUOROMETHYL)SULFENE, (CF3)2C=SO2 - ITS SYNTHESIS AND ISOLATION AS AMINE ADDUCT

被引:9
作者
HARTWIG, U [1 ]
RALL, K [1 ]
SUNDERMEYER, W [1 ]
机构
[1] UNIV HEIDELBERG,INST ANORGAN CHEM,IM NEUENHEIMER FELD 270,W-6900 HEIDELBERG 1,GERMANY
关键词
Sulfene; bis(trifluoromethyl)‐ / Sulfinyl chlorides; trifluoromethyl‐substituted / Sulfonyl chlorides; trifluoromethyl‐substituted;
D O I
10.1002/cber.19901230327
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bis(trifluoromethyl)sulfene, (CF3)2C = SO2: Its Synthesis and Isolation as Amine Adduct Bis(trifluoromethyl)sulfene was obtained and stabilized as quinuclidine adduct 16 by three different methods: (1) by direct symmetrical splitting of the tetrakis(trifluoromethyl)‐1,3‐dithietane S‐oxides 11 and 18 as well as via the TAS salt 15. The structure of 16 exhibits a C–S double bond. The quinuclidinium sulfonate 17 is formed under hydrolysis of 16. In comparison, the corresponding pyridinium sulfonate 13 gives evidence also for the intermediate existence of the adduct 12. The sulfonic acid 7 was prepared, but instead of the sulfonyl chloride 5 the sulfonyl chloride 6 was obtained from 7 and PCl5. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
引用
收藏
页码:595 / 598
页数:4
相关论文
共 21 条
[1]  
[Anonymous], 1988, ANGEW CHEM, V100, P979
[2]   A SUPERIOR METHOD FOR PREPARING SULFINYL CHLORIDES [J].
DOUGLASS, IB ;
NORTON, RV .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (05) :2104-&
[3]   BIS-TRIFLUORMETHYL-SULFIN, (CF3)2C=SO [J].
ELSASSER, A ;
SUNDERMEYER, W .
TETRAHEDRON LETTERS, 1983, 24 (21) :2141-2142
[4]   SYNTHESIS AND PROPERTIES OF TETRAKIS(TRIFLUOROMETHYL)-1,3-DITHIETANE S-OXIDES AND BIS(TRIFLUOROMETHYL)SULFINE [J].
ELSASSER, A ;
SUNDERMEYER, W ;
STEPHENSON, DS .
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (01) :116-123
[5]   BIS(TRIFLUOROMETHYL)SULFINE, (SOF3)2 - NEW SYNTHESES AND SOME REACTIONS [J].
ELSASSER, A ;
SUNDERMEYER, W .
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (11) :4553-4560
[6]  
HARTWIG U, 1988, Z NATURFORSCH B, V43, P271
[7]   AMINE-STABILIZED SULFENES, THEIR SYNTHESIS AND STRUCTURE [J].
HARTWIG, U ;
PRITZKOW, H ;
SUNDERMEYER, W .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (08) :1435-1439
[8]   BIS(TRIFLUOROMETHYL)SULFENE (CF3)2C=SO2, ISOLATED AS ADDUCT [J].
HARTWIG, U ;
PRITZKOW, H ;
RALL, K ;
SUNDERMEYER, W .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (02) :221-223
[9]  
HARTWIG U, 1988, THESIS U HEIDELBERG
[10]  
HARTWIG U, 1989, ANGEW CHEM, V101, P224