6533b85afe1ef96bd12b8ca7

RESEARCH PRODUCT

An unexpected ring carboxylation in the electrocarboxylation of aromatic ketones

Maria Antonietta SabatinoM.p. PaternostroGiuseppe FilardoAlessandro GaliaCarmelo BelfioreOnofrio Scialdone

subject

inorganic chemicalschemistry.chemical_classificationAddition reactionKetoneorganic chemicalsGeneral Chemical EngineeringReaction intermediateSettore ING-IND/27 - Chimica Industriale E TecnologicaHydrogen atom abstractionchemistry.chemical_compoundMeta-chemistryCarboxylationElectrochemistryOrganic chemistryElectrocarboxylationRing carboxylationKetonesCarbon dioxideUndivided cellsBenzoic acidAcetophenone

description

The electrocarboxylation of various aromatic ketones, carried out in N-methyl-2-pyrrolidone (NMP) in a diaphragmless cell equipped with a carbon cathode and an aluminium sacrificial anode, yielded, among the products, the target hydroxy acids, the corresponding alcohols and pinacols and, quite surprisingly, detectable amounts of substituted benzoic acids and cycloexene carboxylic acids. These compounds arise from a never reported before electrocarboxylation on the aromatic ring, respectively, for substitution of an aromatic hydrogen and from an addition reaction. For example, the electrocarboxylation of acetophenone gave rise to the substituted benzoic acids in ortho, para and meta positions, while for 2,2-dimethylpropiophenone the substituted benzoic acid in meta position and the cyclohex-5en-1,3-dicarboxylic acid derivative were detected among the products.

10.1016/j.electacta.2005.09.044http://hdl.handle.net/10447/8424