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The intramolecular C-H insertions of carbenes derived from 2-diazo-2-sulfamoylacetamides were studied. 2-Diazo-2-sulfamoylacetamides were first prepared from chloroacetyl chloride and secondary amines through acylation followed by sequential treatments with sodium sulfite, phosphorus oxychloride, secondary amines, and 4-nitrobenzenesulfonyl azide. The results indicate that: (1) 2-diazo- N,N -dimethyl-2-( N,N -diphenylsulfamoyl)acetamide can take the formal aromatic 1,5-C-H insertion in its N -phenylsulfonamide moiety to afford the corresponding 1,3-dihydrobenzo[ c ]isothiazole-3-carboxamide 2,2-dioxide derivative; (2) no aliphatic C-H insertions occur for 2-diazo-2-( N,N -dialkylsulfamoyl)acetamides; and (3) for 2-diazo- N -phenyl-2-( N -phenylsulfamoyl)acetamides, the formal aromatic 1,5-C-H insertion in the N -phenylacetamide moiety is favorable to afford the corresponding 3-sulfamoylindolin-2-one derivatives as sole or major products. The intramolecular competitive aromatic 1,5-C-H insertion reactions of 2-diazo-2-sulfamoylacetamides with aryl groups on both amide and sulfonamide groups reveal that the N -aryl substituents on acetamide are more active than those on sulfonamide. The chemoselectivity is controlled by electronic effect of the aryl group.

Intramolecular Carbene C-H Insertion Reactions of 2-Diazo-2-sulfamoylacetamides