Quinolinium Dichromate Oxidations. Kinetics and Mechanism of the Oxidative Cleavage of Styrenes

Article abstract of DOI:10.1021/jo00070a031

The kinetics of oxidation of styrene and substituted styrenes by quinolinium dichromate (QDC) in dimethyl formamide, in the presence of acid, has been investigated.The rate of the reaction is dependent on the first powers of the concentrations of substrate, oxidant, and acid.A small inverse kinetic isotope effect has been observed (k_H/k_D = 0.80).Correlation with ? yielded a ρ value of -4.0, suggesting the formation of a cationic intermediate in the rate-determining step of the reaction.Subsequent cleavage of the carbon-carbon bond yielded benzaldehyde and formaldehyde.