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10.15.4.2.4.3.1 Method 1: Replacement of a Diazonium Group by Chlorine (Sandmeyer Reaction)

DOI: 10.1055/sos-SD-010-00864

Gallagher, P. T.Science of Synthesis, (200110736.

The most commonly displaced carbazole functionality has been that of the diazonium group. Thus, halogen and hydroxy functionality have all been introduced from amines via diazonium halides.[‌141‌‌143‌] The treatment of the diazonium salts derived from aminocarbazoles (e.g., 138) with copper(I) chloride results in chlorocarbazoles (e.g., 139; Scheme 68). This is an example of the Sandmeyer reaction, but in the case of diaminocarbazoles the yields are only moderate.[‌144‌]

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