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DOI: 10.1055/sos-SD-031-01513

Rück-Braun, K.; Priewisch, B.Science of Synthesis, (2007311341.

The oxidation of substituted anilines by peracetic acid, or a mixture of glacial acetic acid and 30% hydrogen peroxide, is another convenient method for the preparation of nitrosobenzenes.[‌81‌] This approach is especially useful in the case of 2,6-disubstituted anilines 63, where better yields of the corresponding nitrosoarenes 64 can often be obtained employing peracetic acid (Scheme 33)[‌81‌‌83‌] rather than Caro's acid. The reactions are carried out at room temperature or by gently heating the reaction mixture up to 80°C; however, when the substrates are highly hindered the reaction at room temperature may require up to 14 days to complete. Even so, several 3,5-disubstituted 4-nitrosobenzenesulfonic acids, valuable as spin traps, can be prepared by this method.[‌82‌,‌83‌]

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