Benzylic nitroalkylation by paired electrolysis of benzyl sulfides in nitroalkanes

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• 作者：Shokaku Kim ; Rikiya Uchiyama ; Yoshikazu Kitano ; Masahiro Tada ; Kazuhiro Chiba ; ^{chiba@cc.tuat.ac.jp}
• 关键词：Nitroalkylation ; Paired electrosynthesis ; Lithium perchlorate ; Nitromethane ; Sulfide ; Dithioacetal
• 刊名：Journal of Electroanalytical Chemistry
• 出版年：2001
• 出版时间：13 July 2001
• 年：2001
• 卷：507
• 期：1-2
• 页码：152-156
• 全文大小：136 K

文摘

Benzylic nitroalkylation was accomplished by the paired electrolytic reaction of varied benzyl phenyl sulfides and nitroalkanes in the presence of lithium perchlorate. Benzyl cations were generated by anodic oxidation of the sulfides, and the in situ-generated cationic intermediates were trapped by the cathodic-activated nitroalkyl anion to form the desired nitroalkylated products. Furthermore, electrolysis of benzylic dithioacetals efficiently gave the corresponding carbocations to form the desired nitroalkylated compounds.