26638-45-9Relevant articles and documents
Silver-catalyzed intramolecular oxidative decarboxylative C-H arylation reactions for synthesis of biaryl sultams
Chen, Junmin,Wang, Qiuhong,Li, Xiangkang,Zhao, Yongli
supporting information, p. 105 - 115 (2019/11/11)
A mild, versatile and efficient method to form biaryl sultams through silver-catalyzed intramolecular oxidative decarboxylative C-H arylation reactions has been developed. The present protocol features a broad substrate scope and very good tolerance to di
STRUCTURE AND REACTIVITY IN INTRAMOLECULAR CATALYSIS. CATALYSIS OF SULFONAMIDE HYDROLYSIS BY THE NEIGHBORING CARBOXY GROUP.
Graafland,Wagenaar,Kirby,Engberts
, p. 6981 - 6991 (2007/10/10)
A report is presented on kinetic data for the intramolecular carboxy-catalyzed hydrolysis of 26 sulfonamides in water and in some mixed aqueous solvents. The effective molarity of the carboxyl group is very high (up to ca. 10**8 M) but depends markedly on the structure of the sulfonamide. Substituent effects within a series of 4- and 5-substituted 2-carboxy-N,N-dimethylbenzenesulfonamides are interpreted in terms of nucleophilic catalysis. The role of nonbonded interactions in the initial state and in the transition state is discussed. By using X-ray structural data where available, strain effects have been elucidated for a series of sulfonamides in which the sulfonamide and carboxyl groups are held cis to each other. Striking differences from the corresponding carboxamide systems are attributed to differences in transition state geometries and steric effects.