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31.28.1.33.2 Variation 2: Replacement of an Aromatic C—H Bond by a C—N Bond

DOI: 10.1055/sos-SD-031-01728

Scholz, U.; Schlummer, B.Science of Synthesis, (2007311645.

A very exotic approach to arylamines is the FischerHepp rearrangement[‌365‌] of N-nitrosamines to 4-nitrosoanilines under acidic conditions. N-Nitrosodiphenylamine (182) rearranges to 4-nitroso-N-phenylaniline (15) in 60% yield using diethyl ether saturated with hydrogen chloride at 0°C (Scheme 199).[‌366‌] The methodology can be extended to other systems such as carbazoles.[‌367‌]

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