Rearrangement of Sulfonamide Derivatives. III. Considerations on the Reaction Mechanism.

This is the authors' abstract. We don't add key points for this paper.

Considerations were made on the reaction mechanism of a rearrangement reaction whereby compounds of p- or o-NO2-C6H4-SO2NH-COCH2R type (where R is -COCH3, -CN, -COOR, or -C6H5 group) easily undergo decomposition in the presence of alkali, with liberation of sulfur dioxide to form p- or o-nitrophenylacetamide or its derivatives. It was shown that this reaction is an intramolecular rearrangement and that the me methylene group present must be active in order that this rearrangement reaction proceeds, which was explained by the fact that N-(o-nitrophenylacetyl)-o-nitrobenzenesulfonamide is more reactive than N-phenylacetyl-o-nitrobenzenesulfonamide.