Competitive Pathways in Chlorine Dioxide Oxidation of Amines: Amide Formation from Acyclic Amines.
Abstract
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)
Document Details
- Document Type
- Technical Report
- Publication Date
- Oct 01, 1981
- Accession Number
- ADA107242
Entities
People
- David H. Rosenblatt
- Elizabeth P. Burrows
Organizations
- United States Army Medical Research and Development Command