The anomalous reactivity of the bis(dibutylstannylene) acetal of pentaerythritol: a case of triple activation

The only dibutyltin derivative of pentaerythritol which is observed by refluxing with dibutyltin oxide in methanol is a bis(dibutylstannylene) acetal. This is converted to the expected dibenzyl ether with benzyl bromide, in the presence of tetraethylammonium bromide in boiling toluene, but benzoylation at room temperature gives a tribenzoate. A mechanism is suggested to account for this triple activation.