304-81-4Relevant articles and documents
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Oae,S. et al.
, p. 546 - 552 (1965)
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Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds
Sheng, Jinyu,He, Ru,Xue, Jie,Wu, Chao,Qiao, Juan,Chen, Chao
supporting information, p. 4458 - 4461 (2018/08/09)
The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.
Photochemical Reaction of 2,4-Dinitrodiphenylacetamide and Related Compounds: Spectroscopic and Chemical Identification of Intermediates
Fasani, Elisa,Mella, Mariella,Albini, Angelo
, p. 2689 - 2692 (2007/10/02)
2,4'-Dinitrodiphenylacetamide 1b reacts via the triplet state to give 3-nitrophenazine 5-oxide 2b.The initial step is addition of the nitro group to the C=O bond.This intermediate 7 rearranges in the ms time scale to yield an O-acylnitro derivative 8.This, in turn, undergoes heterocyclic cleavage (rate dependent upon solvent polarity) and the aminium cation thus formed cyclizes to 2b.Intermediate 7 is sensitive to acid-catalysed hydrolysis, and the cleavage of 8 and subsequent cyclization are influenced by various additives.Thus, with triphenylphosphine a phosphoranylidenamino derivative is obtained, and 2,6-di-tert-butylphenol gives 4-nitro-2-nitrosodiphenylamine.Two other amides are compared.
ELECTROGENERATED CATION RADICALS OF HETEROAROMATIC N-OXIDES AND OXIDATION OF CYCLOHEXANE INDUCED BY THEM
Koldasheva, E. M.,Geletii, Yu. V.,Yanilkin, V. V.,Strelets, V. V.
, p. 886 - 890 (2007/10/02)
The primary products of electrooxidation of heteroaromatic N-oxides are the corresponding cation-radicals.The redox properties of N-oxides, and also the stability of the cation-radicals generated from them, are determined by the number of N atoms and N-oxide groups in the heterocyclic ring and also by the nature of the substituents.Using phenazine di-N-oxide as an example, it was shown that the generation of the cation radical induces the oxidation of cyclohexane into cyclohexanol and cyclohexanone and is accompanied by deoxygenation of the di-N-oxide into a mono-N-oxide.The oxidation of cyclohexane proceeds by two paths, in one of which molecular oxygen participates, while in the second path an oxygen transfer probably takes place from the di-N-oxide cation radical to cyclohexane.
