THE REACTION OF XEF2 WITH TRIALKYLVINYLSTANNANES - SCOPE AND SOME MECHANISTIC OBSERVATIONS

Citation
Ma. Tius et Jk. Kawakami, THE REACTION OF XEF2 WITH TRIALKYLVINYLSTANNANES - SCOPE AND SOME MECHANISTIC OBSERVATIONS, Tetrahedron, 51(14), 1995, pp. 3997-4010
Citations number
66
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
51
Issue
14
Year of publication
1995
Pages
3997 - 4010
Database
ISI
SICI code
0040-4020(1995)51:14<3997:TROXWT>2.0.ZU;2-0
Abstract
The combination of a vinylstannane with xenon difluoride in the presen ce of silver(I) triflate results in a very rapid process leading to th e corresponding vinyl fluoride. The reaction is regio- and stereospeci fic and does not require stoichiometric Ag(I). No evidence could be ob tained of radical intermediates on the reaction pathway leading to the vinyl fluorides. A symmetrical dimer derived from the vinylstannane, which was obtained as a reaction byproduct, was shown to arise from ox idative coupling by the silver salt. The results are consistent with a n electrophilic mechanism following an initial interaction of the viny lstannane with Ag(I).