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首页> 外文会议>Fifth International Manuel M.Baizer Symposium in Honor of Professor Jean Michel Saveant at the 201st Meeting of the Electrochemical Society Centennial Meeting May 12-17, 2002 Philadelphia, PA, USA >REDUCTION OF A 'CATION POOL'. A NEW APPROACH TO RADICAL MEDIATED C-C BOND FORMATION
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REDUCTION OF A 'CATION POOL'. A NEW APPROACH TO RADICAL MEDIATED C-C BOND FORMATION

机译：减少“阳离子池”。自由基介导的C-C键形成的新方法

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Carbocations, carbon radicals, and carbanions are important reactive carbon intermediates in organic chemistry and their interconversions can be carried out by redox processes. Although, such relationships have been well recognized, experimental work has been limited to analytical studies on highly stabilized intermediates. In this study such interconversions were examined using electrochemical reduction of "cation pools". N-Acyliminium cations, which were generated by low temperature electrolysis of carbamates, were reduced electrochemically in the absence of radical acceptors. The homo-coupling products formed effectively suggesting that the one-electron reduction of the N-acyliminium cation produced the corresponding, carbon-centered radical. Next, the electrochemical reduction of the N-acyliminium cations in the presence of electron-deficient olefins was examined. The cross-coupling products were obtained in good to moderate yields. A mechanism involving radical addition to the double bond followed by the reduction of the resulting radical to the carbanion was suggested.
机译：碳阳离子，碳自由基和碳负离子是有机化学中重要的反应性碳中间体，它们的相互转化可以通过氧化还原过程进行。尽管已经很好地认识到这种关系，但是实验工作仅限于对高度稳定的中间体进行分析研究。在这项研究中，使用“阳离子池”的电化学还原检查了这种相互转化。在不存在自由基受体的情况下，通过电化学还原氨基甲酸酯的低温电解生成的N-酰基亚胺阳离子。有效形成的均质偶合产物表明，N-酰基亚胺阳离子的单电子还原产生了相应的以碳为中心的自由基。接下来，研究了在缺电子烯烃的存在下N-酰基酰亚胺阳离子的电化学还原。以良好至中等的产率获得了交叉偶联产物。有人提出了一种机制，其中涉及在双键上加成自由基，然后将所得的自由基还原成碳负离子。

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