Mechanistic studies of fluoride-promoted silicon elimination in β-benzotriazolyl-β-aryl-γ-ketosilanes

AR Katritzky, MV Voronkov, D Toader

Index: Katritzky, Alan R.; Voronkov, Michael V.; Toader, Dorin Journal of the Chemical Society. Perkin Transactions 2, 1998 , # 11 p. 2515 - 2518

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Abstract

Vicinal elimination of trimethylsilyl and benzotriazolyl groups from 2-benzotriazolyl-2-aryl-3- ketopropylsilanes forms, along with the expected 1, 1-disubstituted ethylenes, significant amounts of the corresponding chalcones. A study of this transformation by carbon labeling suggests the intermediate formation of cyclopropanes. Stabilizing/destabilizing (electron- donor/acceptor) para-substituents on the aryl group affect the product distribution of the ...