Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

LA Paquette, WE Fristad, DS Dime…

Index: Paquette, Leo A.; Fristad, William E.; Dime, David S.; Bailey, Thomas R. Journal of Organic Chemistry, 1980 , vol. 45, # 15 p. 3017 - 3028

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Citation Number: 133

Abstract

A general method is described for the formation of vinylsilanes from ketones. Thus, conversion to the benzene-or p-toluenesulfonylhydrazone and sequential treatment with n- butyllithium and chlorotrimethylsilane in anhydrous tetramethylethylenediamine proceeds regiospecifically to afford the less substituted vinylsilane (in unsymmetrical cases). FriedelCrafts acylation with acryloyl chlorides and aluminum chloride and subsequent ...