Sulfonyl azides Sulfoxides

Kwart and Kahn have found that benzenesulfonyl azide forms a complex with freshly reduced copper powder.189 190 This copper azide complex decomposes at a lower temperature than the pure sulfonyl azide. In refluxing methanol, benzene-sulfonamide (27) is isolated as the major product. In the presence of dimethyl sulfoxide, N-benzenesulfonyldimethyl-sulfoximine (28) is obtained in almost quantitative yield. In cyclohexene solution benzenesulfonamide (29), N-benzenesul-fonyl-7-azabicyclo[4.1.0]heptane (30), and 1-cyclohexenylben-zenesulfonamide (31) are isolated as the main reaction products. According to the authors, Schemes VII and VIII represent an acceptable interpretation of the experimental data.189 190 In pure alcohol, the decomposition should occur by two competitive reactions (Scheme VII) producing benzenesulfonamide together with a ketone and oxidized copper. These last two products have indeed been observed in the reaction mixture. In the presence of DMSO, it seems that a copper-nitrene intermediate is formed which is trapped by DMSO. In cyclohexene solution, the authors have observed that the aziridine (30) disappears from the product composition when DMSO is added. The yield of enamine 31, however, is... 

Suberic acid, 506 Substrate analogs, 8, 9 Subtilisin, 22, 27, 75, 206, 207 Subtilisin BPN, 215 Succinimide esters, 96 Sucrase-isomaltase complex, 377,379 Suicide reagents, 9, 10 Sulfonyl azides, 78 a-Sulfonyl nitrenes, 78 Sulfoxides, 135... 

Of, jd-Unsaturated Sulfonyl Azide Sulfonyl Chloride Sulfoxide -Sultam Thiazole... 

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