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An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism
Author(s) -
Tang Li,
Wang ZhiLv,
He YanHong,
Guan Zhi
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202001553
Subject(s) - beckmann rearrangement , heteroatom , electrosynthesis , chemistry , electrolysis , electrochemistry , reaction mechanism , rearrangement reaction , photochemistry , computational chemistry , organic chemistry , oxime , catalysis , ring (chemistry) , electrode , electrolyte
Abstract : Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e . the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans ‐migration rule of the classical Beckmann rearrangement.