Substitution at saturated carbon. Part 24. The reactivity of the benzyltin group towards mercury (II) salts in methanol

Abstract

In the reaction of the compounds PhCH₂SnR₃ with mercury(II) salts in methanol, only the benzyl group is cleaved from tin to form PhCH₂HgX when R = Buⁿ, Prⁿ and Et. With PhCH₂SnMe₃, only the methyl group is removed to yield MeHgX. Rate constants are reported for the reaction of PhCH₂SnR₃ with mercury(II) chloride and acetate in methanol, and together with previous work yield the following sequence of reactivity of RSn groups towards mercury(II) chloride and acetate in methanol: R = Ph (1.4 × 10⁵) > Me (430) > PhCH₂(11) > Et(1) > Prⁿ(0.19) > Buⁿ(0.17).