Studies in group VI organometallic chemistry XXV. Necleophilic trans-addtition of organotin hydrides to carbon — carbon triple bonds

Abstract

Mechanistic aspects of the hydrostannation of electrophilic ethynes have been studied. As appears from stereochemical data, kinetics, and substituent, solvent and isotope effects, the addition reaction proceeds by a trans-mechanism in which nucleophilic attack of the hydride hydrogen on carbon is the first and rate-determining step.

In the hydrostannation of diethyl ethynedicarboxylate most probably a five-membered cyclic transition state is involved.