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Oxidative N-N Bond Formation Versus the Curtius Rearrangement.

Melissa Hohenadel1, Ben Ebel1, Iris M Oppel1

  • 1Institutes of Organic and Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 4, 2024
PubMed
Summary

A retracted study incorrectly claimed N-N bond formation from primary amides. The actual reaction produced urea coupling products via the Curtius rearrangement, not N-N coupled products.

Keywords:
BenzamideCross dehydrogenative couplingCurtius rearrangementOxidative N−N bond formationPIDA

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • A previous study reported the oxidative formation of N-N bonds from primary amides using a hypervalent iodane reagent.
  • This study was subsequently retracted due to a misinterpretation of the reaction mechanism.

Purpose of the Study:

  • To investigate and clarify the reaction pathway of the oxidative formation of N-N bonds from primary amides.
  • To identify the actual products formed under the reported conditions and explain the discrepancy.

Main Methods:

  • Re-evaluation of the reaction conditions described in the retracted study.
  • Utilizing Nuclear Magnetic Resonance (NMR) spectroscopy for structural elucidation.
  • Employing X-ray crystallography to confirm product structures.
  • Developing an alternative synthetic route to verify the findings.

Main Results:

  • The reported N-N coupling products were not formed.
  • The Curtius rearrangement was identified as the predominant reaction pathway.
  • Urea coupling products were obtained instead of the claimed N-N coupled products.
  • NMR and X-ray analysis confirmed the structure of the urea products.

Conclusions:

  • The original claim of N-N bond formation from primary amides was erroneous.
  • The reaction proceeds via the Curtius rearrangement, leading to urea derivatives.
  • Proper identification of reaction mechanisms is crucial in chemical synthesis.