Alkali-metal N,N-diethylcarbamates [M(O2CNEt2); M = Li, Na, or K] undergo N-alkylation with MeI, giving tertiary amine and carbon dioxide, in addition to MI; however, O-alkylation with formation of alkylurethane occurs preferentially in the presence of a polyfunctional complexing agent.
A. Belforte and F. Calderazzo, J. Chem. Soc., Dalton Trans., 1989, 1007 DOI: 10.1039/DT9890001007
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