Abstract
The electrochemical reduction of N-fluoro-N-methylurethan (1a) and N-fluorourethan (2a) in acetonitrile generates the amide anion and a fluoride ion. Both the fluoride and the amide anion can 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 [Formula: see text] (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 or lithium hydride. The α-elimination of F− from [Formula: see text] is much easier than the α-elimination of Cl− from [Formula: see text].
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