90498-83-2Relevant academic research and scientific papers
THE ELECTROCHEMICAL REDUCTION OF N-FLUOROETHANS IN ACETONITRILE. THE GENERATION OF CARBETHOXYNITRENE
Lessard, Jean,Berube, Denis
, p. 768 - 777 (2007/10/02)
The electrochemical reduction of N-fluoro-N-methylurethan (1a) and N-fluorourethan (2a) in acetonitrile generates the amide anion and fluoride ion.Both the fluoride and the amide react with the starting N-fluoroamide either as bases or as nucleophiles.Many products are formed and the coulometric results are low (0.5 to 0.7 F/mol).In the case of NFU (2a), abstraction of the proton on nitrogen both by the urethan anion and the fluoride anion generates the conjugate base EtOCOF (7) which immediately undergoes α-elimination of the fluoride ion to give carbethoxynitrene (11).This nitrene was generated also by treating NFU (2a) with a base such as triethylamine of lithium hydride.The α-elimination of F1- from EtOCOF is much easier than α-elimination of Cl1- from EtOCOCl.
