Electrochemical oxidation of amides of type Ph2CHCONHAr

Tatiana Golub, James Y. Becker

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Anodic oxidation of N-aryl-2,2-diphenylacetamides in acetonitrile undergoes three types of bond-cleavage, one between the benzylic carbon and the carbonyl group, the second between a carbonyl and 'N', and the third between the 'N' atom and aryl group. The selectivity of the cleavage and nature of emerged products is highly dependent on the nature of substituent attached to the aryl group. For example, electron-withdrawing groups direct the benzyl-carbonyl bond-breaking whereas electron-donating substituents favor the N-aryl bond cleavage. The type of products obtained involve benzophenone, 2,2-diphenylacetamide, N-(diphenylmethylene)acetamide, N-(diphenylmethyl)acetamide, α-lactam (1-acetyl-3,3-diphenylaziridin-2-one, as a 1:1 complex with 2,4-dinitroaniline) and aniline derivatives.

Original languageEnglish
Pages (from-to)3906-3912
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number19
DOIs
StatePublished - 21 May 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Electrochemical oxidation of amides of type Ph2CHCONHAr'. Together they form a unique fingerprint.

Cite this