Procedures were developed for the synthesis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides by the reactions of the corresponding N-alkoxy-N-chloro derivatives with sodium carboxylates in MeCN. N-Chloro-N-ethoxy-p-toluenesulfonamide was inert in this reaction. Alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and tert-alkylamines afforded the corresponding N,N-dialkoxy derivatives, whereas alcoholysis of N-acetoxy-N-ethoxybenzamide gave rise to alkyl benzoates.
CITATION STYLE
Shtamburg, V. G., Klots, E. A., Pleshkova, A. P., Avramenko, V. I., Ivonin, S. P., Tsygankov, A. V., & Kostyanovsky, R. G. (2003). Geminal systems 50. Synthesis and alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides. Russian Chemical Bulletin, 52(10), 2251–2260. https://doi.org/10.1023/B:RUCB.0000011887.40529.b0
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