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| - Unusual Head-to-Tail Coupling of Alkyl Benzoates byElectroreduction
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| - The electroreduction of alkyl benzoates in an alcoholic solvent gave unusual head-to-tail coupledproducts. Usual head-to-head coupled products derived from acyloin condensation could not bedetected. The best result (73% yield) was obtained from methyl benzoate using an undivided cellwith an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte.Using an undivided cell, the products cross-coupled with a solvent molecule were obtained asbyproducts. The substitution at the para position of methyl benzoate considerably decreased theyields of the head-to-tail coupled products and increased those of the cross-coupled products. Thepossible mechanism of the head-to-tail coupling is the attack of anion radical, generated from methylbenzoate by one-electron transfer, to another methyl benzoate. The cross-coupled products wereformed by the reaction with carbonyl compound anodically produced from a solvent molecule. Thecross-coupling between methyl benzoate and aromatic aldehydes was also effected by the mixedelectroreduction under the same conditions.
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