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The reaction of XeF2 with trialkylvinylstannanes: Scope and some mechanistic observations

1995; Elsevier BV; Volume: 51; Issue: 14 Linguagem: Inglês

10.1016/0040-4020(95)00141-t

1464-5416

Marcus A. Tius, Joel K. Kawakami,

Porphyrin and Phthalocyanine Chemistry

The combination of a vinylstannane with xenon difluoride in the presence of silver(I) triflate results in a very rapid process leading to the corresponding vinyl fluoride. The reaction is regio- and stereospecific and does not require stoichiometric Ag(I). No evidence could be obtained 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 oxidative coupling by the silver salt. The results are consistent with an electrophilic mechanism following an initial interaction of the vinylstannane with Ag(I).