Mechanistic studies of Ce (IV)-mediated oxidation of β-dicarbonyls: Solvent-dependent behavior of radical cation intermediates

J Jiao, Y Zhang, JJ Devery, L Xu, J Deng…

文献索引：Zhang, Yang; Jiao, Jingliang; Flowers II, Robert A. Journal of Organic Chemistry, 2006 , vol. 71, # 12 p. 4516 - 4520

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被引用次数: 23

摘要

The Ce (IV)-initiated oxidation of synthetically relevant β-diketones and β-keto silyl enol ethers was explored in three solvents: acetonitrile, methylene chloride, and methanol. The studies presented herein show that the rate of reaction between Ce (IV) and the substrates is dependent upon the polarity of the solvent. Thermochemical studies and analysis are interpreted to be consistent with transition state stabilization by solvent being primarily ...