Reduction of nitroarenes, azoarenes and hydrazine derivatives by an organic electron donor

Florimond Cumine, Fabrizio Palumbo, John A. Murphy

Research output: Contribution to journalArticle

2 Citations (Scopus)
3 Downloads (Pure)

Abstract

Reduction of nitrobenzene by excess organic electron donor, 12, affords diphenylhydrazine in a reaction where azobenzene oxide and azobenzene are likely intermediates. No cleavage of the N-N σ-bond is seen under photoactivation conditions, whereas traces are seen under thermal activation. Hydrazone derivatives were prepared to explore the cleavage of N-N σ-bonds; the results show that a low-lying LUMO assists the transition state for accepting an electron, and the stabilisation that the potential fragments from N-N bond cleavage afford to the fragments is important in determining whether cleavage is observed.
Original languageEnglish
Pages (from-to)5539-5545
Number of pages7
JournalTetrahedron
Volume74
Issue number38
Early online date23 Apr 2018
DOIs
Publication statusPublished - 20 Sep 2018

Keywords

  • electron transfer
  • reduction
  • Nitroarene
  • Azoarene
  • super electron donor

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