Electrochemical reduction of N-bromosuccinimide. Reaction mechanism for formation of the succinimidyl radical

…, SD Ross, L Eberson, L Joensson

Index: Barry, John E.; Finkelstein, Manuel; Moore, W. Michael; Ross, Sydney D.; Eberson, Lennart; Joensson, Lennart Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1292 - 1298

Full Text: HTML

Citation Number: 26

Abstract

The electrochemical reduction of N-bromosuccinimide in acetonitrile at a platinum cathode generates the succinimidyl radical in an overall process for which the n value is 1. The succinimide anion, generated by two-electron reduction of N-bromosuccinimide, is an intermediate in this process, and its electron-transfer reaction with the N-bromo imide generates the radical. The intermediacy of the succinimide anion is demonstrated by ...

Related Articles:

Organic reactions in ionic liquids: N-alkylation of cyclic imides with alkyl halides promoted by potassium fluoride

[Hu, Yi; Chen, Zhen-Chu; Le, Zhang-Gao; Zheng, Qin-Guo Journal of Chemical Research, 2004 , # 4 p. 276 - 278]

Selective ammonolysis and aminolysis of dimethyl succinate. Synthesis of optically active N-alkylsuccinimides

[Puertas, Susana; Rebolledo, Francisca; Gotor, Vicente Tetrahedron, 1995 , vol. 51, # 5 p. 1495 - 1502]

First triphenylphosphine promoted reduction of maleimides to succinimides

[Pal, Bikash; Pradhan, Prasun K.; Jaisankar, Parasuraman; Giri, Venkatachalam S. Synthesis, 2003 , # 10 p. 1549 - 1552]

Sleep-inducing N-alkyl-5-[m-(trifluoromethyl) phenyl]-5-hydroxy-2-pyrrolidinones and N-alkyl-3-(trifluoromethyl) cinnamamides

[Houlihan, William J.; Gogerty, John H.; Ryan, Eileen A.; Schmitt, Gemma Journal of Medicinal Chemistry, 1985 , vol. 28, # 1 p. 28 - 31]

Solvent-mediated one-pot synthesis of cyclic N-substituted imides

[Patil, Sambhaji V.; Mahale, Keshao A.; Gosavi, Kirankumar S.; Deshmukh, Ganesh B.; Patil, Nilesh S. Organic Preparations and Procedures International, 2013 , vol. 45, # 4 p. 314 - 320]

More Articles...