Abstract
Abstract The oxidation of lactic acid, mandelic acid, and ten monosubstituted mandelic acids by benzyltrimethylammonium dichloroiodate (BTMACI) in glacial acetic acid leads to the formation of the corresponding oxo acid. The reaction is first order with respect to hydroxy acid, BTMACI, and zinc chloride. An addition of benzyltrimethylammonium chloride enhances the rate slightly. [PhCH2Me3N]+[IZn2Cl6]− is postulated to be the reactive oxidizing species. The oxidation of α-deuteriomandelic acid exhibited the presence of a substantial kinetic isotope effect (kH/kD = 5.97 at 298 K). The rate of oxidation of the substituted mandelic acids showed an excellent correlation with Brown’s σ+ values. The reaction constants are negative. A mechanism involving the transfer of hydride ion to the oxidant is postulated.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.