200123-90-6Relevant articles and documents
Soft-Hard Acid/Base-Controlled, Oxidative, N-Selective Arylation of Sulfonanilides via a Nitrenium Ion
Maiti, Saikat,Mal, Prasenjit
, p. 1340 - 1347 (2018)
In iodine(III)-catalyzed, dehydrogenative arylations of sulfonanilides, the functionalization of C-C bonds is preferred over the functionalization of C-N bonds. Herein, an unprecedented N-selective arylation of sulfonanilides using soft-hard acid-base (SHAB) control by a nitrenium ion over a carbenium ion is reported. Treatment of sulfonanilides with iodine(III) led to the formation of nitrenium ions (soft), which preferentially react with biphenyls (soft) over bimesityl (hard) to generate C-N bonds. The iodine(III) was generated in situ by using PhI and mCPBA at room temperature.
Nitration and Bromination of N-(dimethylphenyl)methanesulfonamides
Al-Khafaji, Sarah,Cardinale, Nina,Hanson, James R.
, p. 701 - 714 (2007/10/03)
The orientation of the products of nitrosation: nitration and bromination of the methanesulfonamides of the six isomeric dimethylanilines have been established by 1H NMR nuclear Overhauser experiments.