3-Benzoylpropionic acid, oxidation

The oxidation of substituted /3-benzoylpropionic acids by PFC follows the Hammett relation with a negative reaction constant. A possible mechanism for the oxidation has been discussed.5 The oxidation of maleic, fumaric, crotonic, and cinnamic acids by PCC is of first order with respect to PCC and the acid. The oxidation rate in 19 organic solvents has been analysed by Kamlet s and Swain s multiparametric equations. A mechanism involving a three-centre transition state has been postulated.6 The relative reactivity of bishomoallylic tertiary alcohols toward PCC, to yield substituted THF products via the tethered chromate ester, is dependent only on the number of alkyl groups. This observation suggests a symmetrical transition state in this intramolecular Cr(VI)-alkene reaction.7 Mechanisms have been proposed for the oxidation of 2-nitrobenzaldehyde with PBC8 and of crotonaldehyde with tetraethylammonium chlorochromate.9... 

The Al-chlorobenzamide (NCB) oxidized 3-benzoylpropionic acid (BRA) in AcOH-H2O-HCIO4 to the corresponding carboxylic acid. The reaction was first order in BRA, NCB, and H+ ion, and H2O+CI ion was the reactive species. Added benzamide decreased the rate, and lowering of the dielectric constant increased the rate. ... 

The s)mtheses of some 3,5-diphenyl-3-pyrroIin-2-one derivatives (300) from a-phenyl-i5-benzoylpropionic acids have been reported. Oxidation of these pyrrolinones with various reagents was also investigated. 

---