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

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.

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