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Synlett 2001; 2001(Special Issue): 0964-0966
DOI: 10.1055/s-2001-14634
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Stereochemical Control of the Reaction of Chlorosilane with Methyllithium by the Addition of Metal Cyanide: Inversion by Potassium Cyanide and Retention by Copper(I) Cyanide

Kohei Tamao* , Hayato Tsuji, Akio Toshimitsu
  • *Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan; Fax + 81 774 38 31 86; E-mail: tamao@scl.kyoto-u.ac.jp
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Publication Date:
31 December 2001 (online)

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In the 1,4-dichlorotetrasilane derivative composed of disilane units bearing two pentamethylene tethers, the substitution of a chlorine atom on the silicon atom by the methyl group during the reaction with methyllithium mainly proceeds with inversion of configuration of the silicon atoms, (1) the yield being dramatically improved by the addition of potassium cyanide, and (2) the stereochemistry being changed to retention configuration by the addition of copper(I) cyanide.

bicyclic compounds - copper(I) cyanide - organosilicon compounds - potassium cyanide - stereoselectivity