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

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Cumine, Florimond and Palumbo, Fabrizio and Murphy, John A. (2018) Reduction of nitroarenes, azoarenes and hydrazine derivatives by an organic electron donor. Tetrahedron, 74 (38). pp. 5539-5545. ISSN 0040-4020 (https://doi.org/10.1016/j.tet.2018.04.069)

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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.

ORCID iDs

Cumine, Florimond ORCID logoORCID: https://orcid.org/0000-0003-0158-7387, Palumbo, Fabrizio and Murphy, John A.;
CORE (COnnecting REpositories)