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

Florimond Cumine, Fabrizio Palumbo, John A. Murphy

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.
LanguageEnglish
Pages5539-5545
Number of pages7
JournalTetrahedron
Volume74
Issue number38
Early online date23 Apr 2018
DOIs
Publication statusPublished - 20 Sep 2018

Fingerprint

hydrazine
hydrazines
cleavage
Electrons
Derivatives
Hydrazones
Electron transitions
Oxides
electrons
Stabilization
Hot Temperature
Chemical activation
fragments
hydrazones
nitrobenzenes
stabilization
activation
oxides
azobenzene

Keywords

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

Cite this

Cumine, Florimond ; Palumbo, Fabrizio ; Murphy, John A. / Reduction of nitroarenes, azoarenes and hydrazine derivatives by an organic electron donor. In: Tetrahedron. 2018 ; Vol. 74, No. 38. pp. 5539-5545.
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Reduction of nitroarenes, azoarenes and hydrazine derivatives by an organic electron donor. / Cumine, Florimond; Palumbo, Fabrizio; Murphy, John A.

In: Tetrahedron, Vol. 74, No. 38, 20.09.2018, p. 5539-5545.

Research output: Contribution to journalArticle

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AU - Palumbo, Fabrizio

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KW - electron transfer

KW - reduction

KW - Nitroarene

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KW - super electron donor

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