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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Reaction of Highly Hindered Silicon Halides with Nucleophiles

Janine K. Galligan, D. Alan R. Happer and Gareth R. S. Wilson

Australian Journal of Chemistry 57(5) 497 - 502
Published: 07 May 2004

Abstract

(Me3Si)3CSi(CD3)2I, (Me3Si)3CSi(CD3)2Br, and (Me3Si)3CSi(CD3)2H solvolyze in refluxing acetic acid in the presence of HgX2 to give, in addition to (Me3Si)3CSi(CD3)2X and (Me3Si)3CSi(CD3)2OAc, isomers with structures (Me3Si)2C(SiMe2X)Si(CD3)2Me and (Me3Si)2C(SiMe2OAc)Si(CD3)2Me. The first two also react if AgX is used in place of HgX2, but (Me3Si)3CSi(CD3)2H is inert. In refluxing trifluoroacetic acid (Me3Si)3CSi(CD3)2I and (Me3Si)3CSi(CD3)2H solvolyze even in the absence of a catalyst to give similar products. The products distributions are believed to arise from nucleophilic attack on a methyl-bridged cationic intermediate.

https://doi.org/10.1071/CH03209

© CSIRO 2004

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