• Title/Summary/Keyword: PCC oxidation

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Kinetics and Mechanism of Oxidation of Styryl Biphenyl and Styryl Fluorenyl Ketones by Pyridinium Chlorochromate

  • 성대동;P. Ananthakrishna Nadar
    • Bulletin of the Korean Chemical Society
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    • v.20 no.12
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    • pp.1487-1492
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    • 1999
  • 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.

Michaelis-Menten Behaviour in the Oxidation of Benzaldehydes by Pyridinium Chlorochromate (Corey's Reagent)

  • Ganesh P. Panigrahi;Sasananda Padhy
    • Bulletin of the Korean Chemical Society
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    • v.13 no.5
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    • pp.547-550
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    • 1992
  • The oxidation of benzaldehyde, 3,4-dimethoxy benzaldehyde, p-methoxy benzaldehyde, m-$NO_2$-benzaldehyde, and m-chlorobenzaldehyde by pyridinium chlorochromate (Corey's reagent) are reported. Michaelis-Menten behaviour is observed. The rate determining step appears to be the decomposition of a complex of benzaldehyde with PCC either through a loss of $H^+$ or $H^-$ ions.

A Convergent Synthesis of (Z)-13-Octadecen-1-yl Acetate, the Pheromone Mimic of the Rice Leaf Folder Moth and Its Biological Activity Test

  • Kang Suk-Ku;Moon Byoung-Ho;Lee Jeang-Oon;Goh Hyun-Gwan
    • Bulletin of the Korean Chemical Society
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    • v.6 no.4
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    • pp.228-230
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    • 1985
  • (Z)-13-Octadecen-1-yl acetate, the pheromone mimic of the Rice Leaf Folder Moth, Cnaphalocrosis medinalis, was synthesized from 1,13-tridecanediol in three steps. Monoacetylation of 1,13-tridecanediol followed by PCC oxidation gave 13-acetoxytridecan-1-al. Wittig olefination of the 13-acetoxytridecan-1-al with pentylidenetriphenylphosphonium ylide afforded (Z)-13-octadecen-1-yl acetate, the pheromone mimic of the Rice Leaf Folder.