114526-99-7Relevant academic research and scientific papers
The electrochemical oxidation of silver and tetraethylammonium salts of formamides and imides. N,N-Coupling of formanilidyl radicals
Huot, Jean-Yves,Serve, Denis,Desjardins, Sylvie,Lessard, Jean
, p. 35 - 44 (2007/10/02)
The electrochemical oxidation of Ag, Et4N, and Et4N salts of imides and formanilides, in acetonitrile containing tetraethylammonium tetrafluoroborate, at platinum and vitreous carbon electrodes, is a one-electron and irreversible (αn 1) process leading to an amidyl radicals that preferentially abstracts hydrogen from the medium to give the parent amide.N,N-Coupling (formation of hydrazine derivatives) was observed in the oxidation of the amide-Ag-amide anions of formanilide and p-methoxyformanilide.No coupling was observed in the oxidation of the amide-Ag-amide anion of p-cyanoformanilide and of imides, and in the oxidation of any of the tetraaethylammonium salts (amidyl anions) studied.The formanilidyl radical was trapped by N-tert-butyl-α-phenylnitrone.Attempts to trap the succinimidyl radical by addition to olefins were unsuccessful.
