KINETICS AND MECHANISM OF IODODESTANNYLATION OF STANNATRANES

Article abstract of DOI:10.1016/0022-328X(86)80278-9

A detailed kinetic study of iododestannylation of phenylstannatranes is reported.Reaction rates were compared with reference systems PhSnBu3, PhSn(OMe)3.No evidence was found for iodide catalysis.The reaction is interpreted as involving rate determining Sn-C bond fission.Rates for the stannatranes are some seven times greater than those for PhSn(OMe)3 indicative of increased Sn-N coordination in the transition state.Salt effects were significantly smaller for the stannatranes commeasurate with decreased charge on the electrofugal tin.For PhSn(OMe)3, the reaction was followed in the absence of iodide ion, enabling the evaluation of the association constant for the species <(MeO)3Sn>⁺I^- formed during the reaction.