Mechanisms for the cleavage of carbon-tin bonds. VI. A kinetic and stereochemical study of the halodemetallation of cyclopropyltrialkyltins: the solvent effect

Article abstract of DOI:10.1016/S0022-328X(00)88291-1

The bimolecular halodemetallation of substituted cyclopropyltrialkyltins is stereospecific, and proceeds with retention of the configuration at carbon in methanol, acetic acid and chlorobenzene. The kinetic study confirms the hypothesis which was based on results for the R′SnR₃ series, and shows the participation of the ring orbitals in the rate determining step of the reaction. A study of the selectivity in various media has revealed a surprising solvent effect.