Electron transfer reactions of piperidine aminoxyl radicals

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• 作者：Fa Zhang (1)
  YouCheng Liu (2)
  
• 关键词：aminoxyl radical ; nitroxide ; nitroxyl radical ; iminoxyl radicals ; oxoammonium salt ; electron transfer ; reduction and oxidation
• 刊名：Chinese Science Bulletin
• 出版年：2010
• 出版时间：September 2010
• 年：2010
• 卷：55
• 期：25
• 页码：2760-2783
• 全文大小：1043KB
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• 作者单位：Fa Zhang (1)
  YouCheng Liu (2)
  
  1. Johnson & Johnson Consumer and Personal Products Worldwide, Skillman, New Jersey, 08558, USA
  2. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China
  
• ISSN：1861-9541

文摘

This review article summarizes the electron transfer reactions of piperidine aminoxyl radicals. Electrochemical studies revealed the single electron transfer nature of piperidine aminoxyl radicals. In solution, piperidine aminoxyl radicals serve as single electron transfer oxidation reagent to react with various biologically interesting molecules such as glutathione, cysteine, ascorbic acid, and amines. The reaction product distribution, reaction kinetics, intermediates, and the reaction features in biological mimic environments including micelles and cyclodextrins were investigated. Oxoammonium salts, the one-electron transfer oxidation products of piperidine aminoxyl radicals, are agents of organic synthesis to selectively generate ketones or di-ketones from alcohols or ketones bearing α-methylene group under mild conditions. The new reactions of oxoammonium salts with aromatic amines, phenols, heterocycles including phenothiazines, papaverine, and bilirubin are also illustrated.