114833-01-1Relevant academic research and scientific papers
Study of the Reaction of Benzoyl Chloride and Sodium Dicarboxylate under Inverse Phase Transfer Catalysis
Wang, Maw-Ling,Ou, Chin-Chou,Jwo, Jing-Jer
, p. 2165 - 2174 (1995)
The reaction of benzoyl chloride (PhCOCl) and sodium dicarboxylate (R(COONa)2) catalyzed by an inverse-phase-transfer catalyst (IPTC) in the two-phase medium H2O/CH2Cl2 was investigated.Pyridine 1-oxide (PNO) was used as the inverse-phase-transfer catalyst.The dicarboxylates, namely oxalate, malonate, maleate, succinate, adipate, nonanedioate, fumarate, phthalate, isophthalate, and terephthalate, were selected for study.In general, the observed mixed products included mono- and bis(benzoyloxycarbonyl) compounds, benzoic anhydride and benzoic acid, depending on the molecular structure of the dicarboxylate ion.Dicarboxylates of four types were classified according to distribution of products.The reaction rate is strongly affected by PhCOCl and R(COONa)2 due to their influence on the distribution of PNO in the organic phase.A mechanistic interpretation of the experimental data is presented.
Formation of Anhydrides by Homogeneous Palladium(II)-Catalyzed Carbonylation of Aryl Halides and Metal Carboxylates
Pri-Bar, Ilan,Alper, Howard
, p. 36 - 38 (1989)
Aryl iodides react with sodium, potassium, or calcium carboxylates and carbon monoxide in N,N-dimethyl-formamide, in the presence of palladium acetate, to give acid anhydrides.The reaction proceeds under mild conditions (50-90 deg C, 2.7 atm), affording anhydrides in reasonable yields.The reaction is applicable to bromobenzene, provided one uses higher temperatures or adds tetrabutylammonium iodide.An acylpalladium carboxylate may be a key intermediate in these reactions.
