Direct transfer of aliphatic and aromatic substituents from organosilatranes to mercury(II) species |
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Authors: | J.Dirk Nies Jon M. Bellama Nava Ben-Zvi |
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Affiliation: | Department of Chemistry, University of Maryland, College Park, MD 20742 U.S.A. |
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Abstract: | The relative reaction rates of several silatranes (derivatives of 2,8.9-trioxa-5-aza- 1-silatricyclo[3.3.3.01,5]undecane) and HgCl2 in acetone-d6to yield the corresponding organomercury compound are of the order of e.g., 5 × 10?1 1 mol?1 sec?1 or slightly less, a rate that is unexpectedly high compared to the essentially inert parent organotrialkoxysilanes. Thus, the apical Si&.zsbnd;C bond of the silatrane is extraordinarily susceptible to direct electrophilic attack by mercury(II). The rates decrease in the order CH2CH, C6H5, p-ClC6H4 > CH3 > CH3CH2, CH3CH2CH2 > C6H11, ClCH2, Cl2CH, CH3CH2O. The effects of varying the solvent and the counterions are noted, and the probable mechanism is discussed. |
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