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.
David
S
S
Institut de Chimie Moléculaire, Université de Paris-Sud, Orsay, France. serdavid@icmo.u-psud.fr
D000080:Acetals / Q000737:chemistry*; D008722:Methods; D009947:Organotin Compounds / Q000737:chemistry*; D011409:Propylene Glycols / Q000737:chemistry*
D000080:Acetals; D009947:Organotin Compounds; D011409:Propylene Glycols; C056189:di-n-butyltin; C008783:pentaerythritol