ELECTROPHILIC VINYLATIONS BY VINYLLEAD TRIACETATES AND TRIBENZOATES GENERATED BY TIN LEAD EXCHANGE

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 beta-dicarbonyl compounds and nitronate salts to give moderate...

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Bibliographic Details
Published inJ. Chem. Soc., Perkin Trans. 1 no. 15; pp. 1911 - 1915
Main Authors PARKINSON, CJ, PINHEY, JT, STOERMER, MJ
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1992
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Science & Technology
DECOMPOSITION
CARBON
ALK-1-ENYL-LEAD TRIACETATES
CATION FORMATION
BETA-DICARBONYL COMPOUNDS
ARYLATION REACTION
Lead Organic compounds
Nitronate
Ketoester
Diketone
Exchange reaction
Electrophilic reaction
Tin Organic compounds
Vinylation
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Summary: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 beta-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.
ISSN:0300-922X
2050-8255
1364-5463
DOI:10.1039/p19920001911