Abstract
Rate constants are reported for iodometallation by I 2/I − of a series of tetraalkyltins, R 4Sn, where R = Me, Et, Pr n, Bu iso, and Pe neo. Together with previous literature results the present work shows that constitutional effects of the alkyl group, R, do not parallel those in typical S N2 reactions of alkyl halides. Kinetic studies of the effect of added foreign nucleophiles on the iododemetallation revealed that the anions N 3 −, ClO 4 −, Cl − and Br - did not take part in any kinetically significant step, although small specific kinetic salt effects were noted. Product analyses showed also that neither Br − nor the solvent methanol were involved in any product determining step. The two-stage mechanism proposed by Mathieu can therefore definitely be excluded for the iododemetallation of tetraalkyltins in methanol and other alcoholic solvents.
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