The medium dependence of the rates of base cleavage of carbon—silicon and—tin bonds |
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| Authors: | Colin Eaborn John R. Jones Giancarlo Seconi |
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| Affiliation: | School of Molecular Sciences, University of Sussex, Brighton BN1 9QJ Great Britain;Department of Chemistry, University of Surrey, Guildford GU2 5XH Great Britain;Laboratorio dei composti del carbonio contenenti eteroatomi e loro applicazioni, C.N.R., Via Tolara di Sotto 89, 40064 Ozzano Emilia, Bologna Italy |
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| Abstract: | Rates of cleavage of Me3MR compounds (M = Si, R = m-ClC6H4CH2, p-NO2C6H4CH2, Ph2CH, 9-fluorenyl, and 2-benzothienyl; M = Sn, R = m-ClC6H4CH2, Ph2CH, 2-benzothienyl) have been measured in Me2SO/MeOH/MeONa, Me2SO/EtOH/EtONa, and Me2SO/H2O/HONMe4 media containing varying amounts of the hydroxylic component. The variations in the slopes of the log krel H plots are consistent with the view that a water or alcohol molecule provides electrophilic assistance in the rate-determining step for the tin compounds with R = m-ClC6H4CH2 and 2-benzothienyl, while for the silicon compounds, and possibly for the tin compound with R = Ph2CH, carbanions are liberated in the rate-determining step. |
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