Pharmaceutical Bulletin
Online ISSN : 1881-1345
Print ISSN : 0369-9471
ISSN-L : 0369-9471
Rearrangement of Sulfonamide Derivatives. III. Considerations on the Reaction Mechanism.
Takeo NaitoRenzo DohmoriMutsuo Shimoda
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1955 Volume 3 Issue 1 Pages 34-37

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Abstract
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.
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© The Pharmaceutical Society of Japan
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