Structure elucidation of a cryptic condensation product from diacetyl and arylamine - Then and now

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Some 70 years ago, the reaction of diacetyl (1) and arylamines (2) in hot phosphoric acid was reported to give a new type of condensation products, but no structure was assigned to them. The case is presented to recapitulate the methods and rationales used in classical structure elucidation of organic molecules through reaction networks, before spectroscopic or crystallographic methods were generally available. The difficulties and limits of the classical approach are exemplified through this real-life problem, which could not be solved by the methodology of its time. A representative condensation product 4a has been resynthesized from 1 and p-toluidine (2a), and its structure elucidation by means of 2D NMR techniques is outlined.

Original languageEnglish
Pages (from-to)293-297
Number of pages5
JournalChimia
Volume74
Issue number4
DOIs
StatePublished - Apr 2020

Keywords

  • Heterocycles
  • History of chemistry
  • NMR spectroscopy
  • Structure elucidation
  • Synthetic methodology

Fingerprint

Dive into the research topics of 'Structure elucidation of a cryptic condensation product from diacetyl and arylamine - Then and now'. Together they form a unique fingerprint.

Cite this