The dehalogenation reaction of organic halides by tributyltin radical: The energy of activation vs. the BDE of the C-X bond

Article abstract of DOI:10.1016/S0040-4020(98)83025-1

The energy of activation (E(a)) of the dehalogenation reaction induced by Bu₃Sn^. was measured for some aryl, alkyl and benzyl halides. BDE values of the C-X bond undergoing homolysis were obtained from thermochemical cycles, and correlated with the E(a) values. No major effect due to the polarity of the C-X bond was found. Durene derivatives showed a buttressing effect. A comparison of the homolytic BDE of the C-X bond of organic halides with the BDE of the C-X bond in the radical anion of the same precursors is reported.