Add time:07/26/2019         Source:sciencedirect.com

Alkylmercuric benzoate and chloride formed in the benzoyl peroxide-initiated reaction of dialkylmercury in carbon tetrachloride solutions arise by homolytic displacements. Kinetic isotope effects demonstrate that any alkylmercuri radicals formed in the concurrent reductive elimination to metallic mercury cannot be intermediates leading to alkylmercuric chloride. Benzoyl peroxide and butyryl peroxide show widely divergent behavior as initiators owing to differences in the stabilities of the acyloxy radicals formed on homolysis, the relatively long-lived benzoyloxy radical being effective in SH2 displacements on dialkylmercury in contrast to propyl radicals derived from the highly unstable butyryloxy radicals. The reactivity of oxygen-centered, chlorine and alkyl radicals are compared in homolytic displacements. A unified mechanism is presented for reductive elimination and the various substitution processes observed concurrently in dialkylmercury compounds, in which the radical intermediates are shared in common.

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