Homolytic organometallic reactions : XII. Homolytic dealkylation of di-n-butyl-t-butyltin chloride: preferential displacement of the n-butyl radical

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t-Butoxyl radicals react with di-n-butyl-t-butyltin chloride to show the ESR spectrum of the n-butyl rather than the t-butyl radical. Cumyloxyl radicals behave similarly, but trimethylsiloxyl and benzoyloxyl radicals react to give both n-butyl and t-butyl radicals. The unexpected preferential formation of the less stable n-alkyl radical is tentatively ascribed to steric constraints in a 5-coordinate intermediate.