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

TETRAHEDRON

卷:74

Article

Cumine, Florimond¹  Palumbo, Fabrizio¹  Murphy, John A.¹ 

[1] Univ Strathclyde, Dept Pure & Appl Chem, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

关键词: Reduction;    Electron transfer;    Nitroarene;    Azoarene;    Super electron donor;   

DOI  :  10.1016/j.tet.2018.04.069

来源: Elsevier

【 摘 要 】

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 sigma-bond is seen under photoactivation conditions, whereas traces are seen under thermal activation. Hydrazone derivatives were prepared to explore the cleavage of N-N sigma-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. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

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