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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 12
BKCSDE 20(12)
December 20, 1999 

Kinetics and Mechanism of Oxidation of Styryl Biphenyl and Styryl Fluorenyl Ketones by Pyridinium Chlorochromate
Dae Dong Sung, P. Ananthakrishna Nadar
The kinetics of oxidation of substituted styryl 4-biphenyl ketones and of substituted styryl 2-fluorenyl ketones by pyridinium chlorochromate (PCC) have been studied in 90% acetic acid- 10% water (v/v) containing perchloric acid and NaClO4 at 10 0 , 20 0 , 30 0 and 40℃. The reactions are first order in styryl ketones and PCC. The second order rate constants are well correlated only with σ+ constants implying development of positive charge adjacent to benzene ring in the transition state. The effects of varying [HClO4] and the percentage of acetic acid on the reactions have also been analysed. A mechanism involving nucleophilic attack of PCC leading to an unsymmetric intermediate from which epoxides are formed is proposed.
1487 - 1492
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