Aromatic sulphonyl azides react readily with unstrained olefins to give imines ⇌ enamines which, on hydrolysis, give the corresponding sulphonamide and ketone. In some cases, rearrangement occurs during the nitrogen elimination step. Reduction of the imines in situ with sodium borohydride leads to the arenesulphonamides in good yield.
R. A. Abramovitch, G. N. Knaus, M. Pavlin and W. D. Holcomb, J. Chem. Soc., Perkin Trans. 1, 1974, 2169 DOI: 10.1039/P19740002169
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