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10.15.1.1.5.2.1 Variation 1: Thermolysis of Azidobiphenyls

DOI: 10.1055/sos-SD-010-00864

Gallagher, P. T.Science of Synthesis, (200110709.

The thermal decomposition of biaryl azides, e.g. 58, gives high yields of substituted carbazoles, e.g. 59 (Table 2). Reaction times are short (<5min) and the products are isolated by simple precipitation. This reaction deserves comparison to the deoxygenation of nitrobiaryls with triethyl phosphite.[‌77‌] The azide decomposition procedure usually involves synthesis of the nitrobiaryl and then conversion to the aryl azide via the aryl amine. These additional steps are probably advisable if high yields of carbazole are needed and purification is to be kept to a minimum, as chromatographic separation is required with the triethyl phosphite syntheses.

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References


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