TY - JOUR
T1 - Electrophilic vinylations by vinyllead triacetates and tribenzoates generated by tin-lead exchange
AU - Parkinson, Christopher J.
AU - Pinhey, John T.
AU - Stoermer, Martin J.
PY - 1992
Y1 - 1992
N2 - 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.
AB - 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.
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U2 - 10.1039/p19920001911
DO - 10.1039/p19920001911
M3 - Article
AN - SCOPUS:37049083739
SN - 1472-7781
SP - 1911
EP - 1915
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 15
ER -