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Issue 16, 1997
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Chromium(II)-mediated synthesis of vinylbis(silanes) from aldehydes and a study of acid- and base-induced reactions of the derived epoxybis(silanes): a synthesis of acylsilanes

Abstract

The synthesis of vinylbis(silanes) 1 from aldehydes and dibromomethylenebis(trimethylsilane) using chromium(II) chloride in DMF is described. Epoxidation of vinylbis(silanes) 1 and treatment of the resulting epoxybis(silanes) 2 with sulfuric acid in methanol gives acylsilanes 3. Mechanistic studies of acylsilane formation, together with a crystal structure of epoxybis(silane) 2 (R = 3,5-dinitrobenzoyloxymethyl) and the finding that 1-halovinylsilanes 7 (X = Cl, Br, I) can be prepared from epoxybis(silanes) 2 using hydrogen halides, all indicate that the preferred site of nucleophilic attack in epoxybis(silanes) 2 is at the disilyl-substituted carbon. Reaction of alkyl-substituted epoxybis(silanes) such as 2b,c with LDA proceeds by an unusual rearrangement process to give silanols 14.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1997, 2279-2290
Article type
Paper

Chromium(II)-mediated synthesis of vinylbis(silanes) from aldehydes and a study of acid- and base-induced reactions of the derived epoxybis(silanes): a synthesis of acylsilanes

D. M. Hodgson, P. J. Comina and M. G. B. Drew, J. Chem. Soc., Perkin Trans. 1, 1997, 2279
DOI: 10.1039/A702722B

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