Reaction of tris(trimethylsilyl)methylsilicon halides with methanolic sodium methoxide. Probability of sila-olefin intermediates |
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Authors: | Colin Eaborn Duncan AR Happer Kazem D Safa |
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Institution: | School of Molecular Sciences, University of Sussex, Brighton BN1 9QJ, Great Britain |
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Abstract: | The compounds TsiSiR2X Tsi = Me3Si)3C; R = Me, X = Cl, Br, I, or R = Ph, X = F, Cl, Br, I)] react with boiling 2 M MeONa-MeOH to give products of the type (Me3Si)2CHSiR2OMe. It is suggested that the reaction proceeds through an elimination, analogous to E2 eliminations of alkyl halides, involving synchronous attack of MeO? at an Me3Si group, liberation of X?, and formation of (Me3Si)2CSiR2. The compounds TsiSiPhMeF TsiSiPhCl2 react analogously to give (Me3Si)2CHSiPhMe(OMe) and (Me3Si)2CHSiPh(OMe)2 tha latter presumably by solvolysis of the initially-formed (Me3Si)2CHSiPhCl(OMe)]. The compounds TsiSiMe2OMe and TsiSiMe3 do not react, while TsiSiMe2H gives TsiH. The compound TsiSiCl3 reacts with 0.1 M MeONa-MeOH to give the substitution and elmination products TsiSiCl2(OMe) and (Me3Si)2CHSi(OMe)3 in ca. ratio. |
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