The chlorination of N-alkoxy-N-alkylureas (1) by the action of t-BuOCl proceeds regiospecifically to give stable N-chloro-N-alkoxy-N'-alkylureas (2). The alcoholysis of 2 leads to N,N-dialkoxy-N'-alkylureas (3). The alkaline hydrolysis of 3 is a new, convenient method for the preparation of dialkoxyamines.
chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C–C bondcleavage. Here, we demonstrate that such pretreatment can be avoided and the C–C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in
N,N-dimethoxyamine; a new methylating, aminating, and epiminating reagent
作者:Vladimir F. Rudchenko、Sergei M. Ignatov、Remir G. Kostyanovsky
DOI:10.1039/c39900000261
日期:——
Electrophilically catalysed cleavage of the N–O bond of N,N-dimethoxyamine results in the formation of singlet N-methoxynitrenium ion, which aminates soft nucleophiles, methylates hard ones, and epiminates alkenes.