Mechanisms of stannyl-carbon bond cleavages by reactions with benzoyl peroxide.
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The mechanism for the process giving trimethyl(benzoyloxy)stannane by the reaction of benzoyl peroxide with trimethylphenylstannane or tetramethylstannane has been investigated. The kinetic results exclude the possibility that the decomposition of the peroxide is induced by the stannanes. The addition of dicyclohexylcarbodiimide as a trapping agent for benzoic acid markedly depressed the yield of the benzoyloxystannane by the reaction of trimethylphenylstannane, suggesting that the benzoyloxystannane is mainly or exclusively produced by the protodestannylation reaction of trimethylphenylstannane with benzoic acid. In the reaction of tetramethylstannane with benzoyl peroxide, trimethyl(benzoyloxy)stannane was formed only when a large excess of the stannane was used, and dicyclohexylcarbodiimide showed no significant effect upon the formation of the benzoyloxystannane. A homolytic process has been suggested for the reaction giving the benzoyloxystannane from tetramethylstannane.
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