Electrophilic vinylations by vinyllead triacetates and tribenzoates generated by tin-lead exchange

Christopher J. Parkinson, John T. Pinhey, Martin J. Stoermer

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Trimethyl(vinyl)stannanes undergo a rapid tin-lead exchange with lead tetraacetate to give high yields of unstable vinyllead triacetates. Solutions of vinyllead triacetates produced in this way react with soft carbon nucleophiles such as β-dicarbonyl compounds and nitronate salts to give moderate to good yields of C-vinylated products. The method is more economical in terms of vinyl group incorporation than previously reported vinylations by vinyllead triacetates. An even faster tin-lead exchange has been observed when trimethyl(vinyl)stannanes are treated with lead tetrabenzoate, and vinylations with this reagent proceeded in significantly higher yields.

Original languageEnglish
Pages (from-to)1911-1915
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number15
Publication statusPublished - 1992

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