Competitive Pathways in Chlorine Dioxide Oxidation of Amines: Amide Formation from Acyclic Amines

摘要

Treatment of dibenzylamine and ethyl N,N-dibenzylglycinate with chlorine dioxide (C1O2) gave, in addition to the expected products of oxidative dealkylation, substantial amounts of amides. With the second reaction and preformed C1O2 at pH 4-7, ethyl N,N-dibenzyloxamate was the predominant isomer; however, with C1O2 generated in situ at pH 2.5-3, ethyl N-benzoyl-N-benzyl glycinate was predominant. In the latter case the combined yield of amides was sufficiently high (80%) to be of synthetic utility. (Author)