Permanganate peroxidation of cyclohexene.I. The unusual effect of turbulent stirring and dilution upon glycol yields
作者:
Jay E. Taylor,
David Williams,
Kenneth Edwards,
Donald Otonnaa,
David Samanich,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1984)
卷期:
Volume 62,
issue 1
页码: 11-15
ISSN:0008-4042
年代: 1984
DOI:10.1139/v84-003
出版商: NRC Research Press
数据来源: NRC
摘要:
Yields ofcis-1,2-cyclohexanediol formed by the reaction of methanol–water solutions of potassium permanganate with cyclohexene varied from nearly zero to a high of 84% as a function of stirring efficiency and dilution. This unusual effect is attributed to the formation of an intermediate hypomanganate ester ion which after formation may undergo reaction [1] with water to form the glycol or [2] with excess MnO4−to form higher oxidation products. The factor of increased stirring and dilution reduced localized excess of MnO4−and, thereby, minimized the contribution of reaction [2]. Addition of modest concentrations of methanol increased the yield, and this is attributed to enhanced solubilization and dispersion of the insoluble cyclohexene. Sodium hydroxide was beneficial to the reaction but only in low concentrations.
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