HALOGEN-CARBON-SULFUR COMPOUNDS - SYNTHESES WITH 2-METHYLTHIO-4,5-BIS(TRIFLUOROMETHYL)-1,3-DITHIOLIUM TRIFLUOROMETHANESULFONATE

被引:12
作者
MONO, S [1 ]
PRITZKOW, H [1 ]
SUNDERMEYER, W [1 ]
机构
[1] UNIV HEIDELBERG,INST ANORGAN CHEM,IM NEUENHEIMER FELD 270,D-69120 HEIDELBERG,GERMANY
来源
CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 09期
关键词
1,3-DITHIOLIUM SALTS, 2-AMINO, 2-METHYLTHIO; REACTIONS WITH PHENOLES AND ACTIVE METHYLENE COMPOUNDS; HYDRATION; 1,3-DITHIOLES; PHOSPHONIUM SALTS; PHOSPHORANES;
D O I
10.1002/cber.19931260922
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
By reactions of the strongly electrophilic 2-methylthio-4,5-bis-(trifluoromethyl)-1,3-dithiol-2-ylium trifluoromethanesulfonate (6) with nucleophiles like secondary amines, phenoles and active methylene compounds the new 2-amino-1,3-dithiolium salts 11a-e and 1,3-dithiol-2-ylidene compounds 5-10, 12 were obtained. The 1,3-dithiolium salts 14 were prepared in two different ways. Reaction with PPh3 yields the phosphonium salt 16, from which the ethylidene compound 20 was obtained via the intermediate phosphorane 18. The crystal structures of 7, 16 and of the fulvalene 19 were determined.
引用
收藏
页码:2111 / 2118
页数:8
相关论文
共 32 条
[1]   SYNTHESIS OF SOME NOVEL TRIFLUOROMETHANESULFONATES AND THEIR REACTIONS WITH ALCOHOLS [J].
BEARD, CD ;
BAUM, K ;
GRAKAUSK.V .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (21) :3673-3677
[2]   ORGANIC METALS [J].
BRYCE, MR ;
MURPHY, LC .
NATURE, 1984, 309 (5964) :119-126
[3]   DITHIOLIUM DERIVATIVES .3. REACTIONS OF 2-METHYLTHIO-4-SUBSTITUTED 1,3-DITHIOLIUM CATION [J].
CAMPAIGNE, E ;
HAMILTON, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) :1711-&
[4]  
CAMPAIGNE E, 1970, QUART REP SULFUR CHE, V5, P275
[5]  
CHAICHIT N, 1981, CRYST STRUCT COMMUN, V10, P83
[6]   2,4,6-TRIS(4,5-DI-NORMAL-PROPYL-1,3-DITHIOL-2-YLIDENE)CYCLOHEXANE-1,3,5-TRIONE - SYNTHESIS, X-RAY CRYSTAL-STRUCTURE AND AMPHOTERIC REDOX PROPERTIES OF A HIGHLY DELOCALIZED HETEROCYCLIC PI-SYSTEM [J].
COFFIN, MA ;
BRYCE, MR ;
CLEGG, W .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (05) :401-402
[7]  
Cooper W. F., 1974, CRYST STRUCT COMMUN, V3, P23
[8]   ALKYLATION REACTIONS OF 4,5-BIS(TRIFLUOROMETHYL)-1,3-DITHIOLE-2-THIONE - A 1ST X-RAY STRUCTURE DETERMINATION OF A 2-ALKYLTHIO-1,3-DITHIOLIUM SALT [J].
FRASCH, M ;
MONO, S ;
PRITZKOW, H ;
SUNDERMEYER, W .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (01) :273-275
[9]   SYNTHESIS AND PROPERTIES OF NEW PI-DONOR SULFUR HETEROCYCLES [J].
HANSEN, TK ;
LAKSHMIKANTHAM, MV ;
CAVA, MP ;
METZGER, RM ;
BECHER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2720-2722
[10]   1,3-DITHIOLIUM CARBENES FROM ACETYLENES AND CARBON-DISULFIDE [J].
HARTZLER, HD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (13) :4379-4387