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KINETICS AND MECHANISM OF OXIDATION OF SECONDARY ALCOHOLS BY MORPHOLINIUM FLUOROCHROMATE

Oxidation of several secondary alcohols by morpholinium fluorochromate (MFC) in DMSO leads to the formation of corresponding ketones.  The reaction is first order each in MFC and acidity. The reaction exhibited Michaelis-Menten kinetics with respect to alcohols. The oxidation of 2-propanol- d 2 (MeCDOHMe) exhibited a substantial primary kinetic isotope effect ( k H / k D = 5.16 at 298 K). The oxidation of 2-propanol has been studied in nineteen different organic solvents. The solvent effect has been analysed using Taft's and Swain's multiparametric equations. The reaction was subject to both polar and steric effects of the substituents. A mechanism involving transfer of hydride ion from alcohol to the oxidant, via a chromate ester, has been proposed.