Substitution at saturated carbon. Part XIII. Steric effects in the substitution of tetra-alkyltin compounds by mercury(II) chloride in t-butyl alcohol and in acetonitrile
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in J. Chem. Soc. A
- p. 2566-2569
- https://doi.org/10.1039/j19710002566
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 > Prn 4Sn Bun 4Sn > Bui 4Sn Pri 4Sn 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.Keywords
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