3871-28-1Relevant articles and documents
Geminal systems: 64. N-alkoxy-N-chloroureas and N,N-dialkoxyureas
Shtamburg,Kostyanovsky,Tsygankov,Shtamburg,Shishkin,Zubatyuk,Mazepa,Kravchenko
, p. 62 - 75 (2015/10/05)
Molecular and crystal structures of N-alkoxy-N-chloroureas and N,N-dialkoxyureas were studied together with those of N-alkoxyureas as reference compounds. N-Alkoxy-N-chloroureas were found to have an elongated N - Cl bond and a shortened N-O(Alk) bond due to the nO(Alk)→σN-Cl anomeric effect. Alcoholysis of N-alkoxy-N-chloro derivatives of urea, N′-arylureas, and carbamates in the presence of silver trifluoroacetate leads to sterically hindered N,N-dialkoxyureas, N,N-dialkoxy-N′-arylureas, and N,N-dialkoxycarbamates, respectively.
Geminal systems 50. Synthesis and alcoholysis of N-acyloxy-N-alkoxy derivatives of ureas, carbamates, and benzamides
Shtamburg,Klots,Pleshkova,Avramenko,Ivonin,Tsygankov,Kostyanovsky
, p. 2251 - 2260 (2007/10/03)
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.