A Practical One-Pot Synthesis of Vinylstannanes from Ketones

Alla Darwish and J. Michael Chong*

*Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry (GWC2), Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1, Email: jmchonguwaterloo.ca

A. Darwish, J. M. Chong, J. Org. Chem., 2007, 72, 1507-1509.

DOI: 10.1021/jo062145f

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Abstract

Treatment of ketones with Bu₃SnLi followed by addition of MsCl/Et₃N to the resulting alkoxide provides vinylstannanes. Traces of Bu₃SnH in the crude reaction products could be removed by stirring in CHCl₃ with a catalytic amount of AIBN followed by filtration through silica gel.

see article for more examples

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Key Words

Vinylstannanes

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ID: J42-Y2007-0610