(Fluorovinyl)trimethylsilanes from the electrochemical silylation of fluoroalkenes in the presence of chlorotrimethylsilane

被引:11
作者
Martynov, BI
Stepanov, AA
Griffiths, DV
机构
[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
[2] State Res Inst Organ Chem & Technol, Moscow 111024, Russia
[3] Univ Essex, Dept Chem & Biol Sci, Colchester CO4 3SQ, Essex, England
关键词
D O I
10.1016/S0040-4020(97)10275-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the 2-substituted (1,2-difluorovinyl)trimethylsilanes 3 (R = F, Cl and CF3) has been investigated by the electrochemical reduction of an appropriate fluoroalkene in the presence of chlorotrimethylsilane (TmsCl) in an undivided cell using a sacrificial anode. While the vinylsilanes 3 (R = F and Cl) were produced in good yield from trifluorobromoethene and 1,2-difluoro-1,2-dichloroethene, respectively, the production of 3 (R = CF3) from hexafluoropropene was only achieved in low yield. Voltammetry data are presented. (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:257 / 262
页数:6
相关论文
共 17 条
[1]  
[Anonymous], IZV NAUK SSSR K
[2]   NEW CONVENIENT ROUTE TO POLYFLUOROALKENYLTRIALKYLSILANES AND GERMANES [J].
BARDIN, VV ;
PRESSMAN, LS ;
CHERSTKOV, VF .
SYNTHETIC COMMUNICATIONS, 1995, 25 (16) :2425-2433
[3]   METAL EXCHANGE BETWEEN AN ELECTROGENERATED ORGANONICKEL SPECIES AND ZINC HALIDE - APPLICATION TO AN ELECTROCHEMICAL, NICKEL-CATALYZED REFORMATSKY REACTION [J].
CONAN, A ;
SIBILLE, S ;
PERICHON, J .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2018-2024
[4]   ORGANOSILICON CHEMISTRY .9. REACTION OF BIS(TRIMETHYLSILYL)-MERCURY WITH SOME POLYFLUORO-OLEFINS [J].
FIELDS, R ;
HASZELDI.RN ;
HUBBARD, AF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (06) :847-&
[5]  
Fleming I., 1979, COMPREHENSIVE ORGANI, V3, P541
[6]  
HAHNFELD JL, 1975, TETRAHEDRON LETT, P773
[7]  
MAGNUS PD, 1982, COMPREHENSIVE ORGANO, V7, P515
[8]  
MARTYNOV BI, IN PRESS J FLUOR CHE
[9]   ELECTROCHEMICAL, NICKEL-CATALYZED REFORMATSKY REACTION WITH METHYL CHLORODIFLUOROACETATE [J].
MCHAREK, S ;
SIBILLE, S ;
NEDELEC, JY ;
PERICHON, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 401 (1-2) :211-215
[10]   SUBSTITUENT EFFECTS ON CHEMICAL SHIFTS AND SPIN-SPIN COUPLING CONSTANTS IN TRIFLUOROVINYL DERIVATIVES [J].
MORELAND, CG ;
BREY, WS .
JOURNAL OF CHEMICAL PHYSICS, 1966, 45 (03) :803-&