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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 11
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Original Articles

Diethylaluminum Chloride Mediated Vinylsilane Synthesis: Comparison of Different Solvent Systems

Man Lung Kwan Department of Chemistry, John Carroll University, University Heights, 20700 N. Park Blvd., Ohio, 44118, USACorrespondence[email protected]
,
Merle A. Battiste Department of Chemistry, University of Florida, Gainesville, Florida, USA
,
Megan K. Macala Department of Chemistry, John Carroll University, University Heights, 20700 N. Park Blvd., Ohio, 44118, USA
,
Sylvia C. Aybar Cuyahoga Community College, Highland Hills, Ohio, USA
,
Nicholas C. James Department of Chemistry, John Carroll University, University Heights, 20700 N. Park Blvd., Ohio, 44118, USA
&
Joseph J. Haoui Department of Chemistry, John Carroll University, University Heights, 20700 N. Park Blvd., Ohio, 44118, USA
Pages 1943-1950 | Received 03 Jan 2004, Published online: 20 Aug 2006
 
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Abstract

Aromatic ketones were converted to one‐carbon elongated‐vinylsilanes in a convenient one‐pot operation via the Peterson protocol. Reactions were conducted in two different solvents for comparison: pentane and triethylamine. Results indicate that triethylamine appeared to be a more suitable solvent for such a transformation producing vinylsilanes with great chemo‐ and stereo‐selectivity than pentane.

Acknowledgements

We would like to thank Drs. Kenneth Doxsee, David Kimball, Michael Zagorski, Dale Ray, and Bruce Branchaud for their valuable suggestions or technical support and Huntington Foundation and National Institute of Health (Bridges to Success in the Sciences Program) for their financial support.

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