Nitroxy radicals that are formed by the reaction of some sterically hindered phenoxyls with nitrosobenzenes

Zhuzhgov, E. L.; Bazhin, N. M.; Terpugova, M. P.; Tsvetkov, Yu. D.

doi:10.1007/bf00922125

Cited by 5 publications

(2 citation statements)

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“…Although the generation of phenoxy radicals resulting from the abstraction of the phenolic H-atom is the dominating radical process during the oxidation, the tendency towards the abstraction of an H-atom from a Me group in 4-methyl-substituted phenols was also observed. The benzyl radicals formed were detected by a spin-trapping technique by using nitroso spin traps [4] [5]. The recombination products of benzyl radicals observed in the reaction mixture of the oxidized phenols also support this mechanism, although other theories interpreting their formation have been proposed [6].…”

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confidence: 89%

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Spin Trapping of Radical Intermediates Generated by the Oxidation of Substituted 4‐Methylphenols

Majzlík

Omelka

Superatová

et al. 2011

Helvetica Chimica Acta

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A series of substituted 4‐methylphenols 1 and 2 was oxidized with PbO2 in the presence of nitroso compounds 3–10. The formation of adducts of benzyl radicals with the nitroso spin traps in the reaction mixture was established, suggesting the abstraction of an H‐atom from the methyl substituent of 1 or 2. In the consecutive steps, the adducts underwent a further rearrangement to the corresponding nitrones. When the starting phenol contained bulky tBu groups in ortho‐position (see 2,6‐di(tert‐butyl)‐4‐methylphenol (1a)), the stable 2,6‐di(tert‐butyl)‐4R‐phenoxy radicals (R=CHN+(O−)X) were detected as the final radical products. The indirect evidence of nitrones in the reaction mixture was performed in one case by the reaction with a RO$\rm{{_{2}^{{^\cdot} }}}$ radicals.

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confidence: 89%

“…Scheme 2 [5]. The concentration ratio between the two radicals 11a and 12a depended on the experimental conditions, and in the presence of an excess of phenol 1a over the spintrap agent 3, the EPR spectrum of the pure benzyl radical adduct 13a was observed ( Fig.…”

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confidence: 94%