Abstract
Rate constants have been determined for the substitution of tetramethyl-, tetraethyl-, tetra-n-propyl-, tetraisopropyl-, tetra-n-butyl-, and tetraisobutyl-tin by mercury(II) chloride in solvents t-butyl alcohol and acetonitrile. With both solvents, the rate constants decrease markedly along the series R4Sn = Me4Sn Et4Sn > Prn4Sn Bun4Sn > Bui4Sn Pri4Sn and thus give rise to the same steric sequence of reactivity found previously for the substitution of tetra-alkyltins by mercury(II) chloride in methanol and methanol–water mixtures. It is concluded that the above substitutions in solvents t-butyl alcohol and acetonitrile proceed by essentially the same mechanism as do the corresponding substitutions in solvents methanol and methanol–water, that is by the SE2(open) mechanism of substitution at saturated carbon.
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More From: Journal of the Chemical Society A: Inorganic, Physical, Theoretical
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