610754-79-5

Basic information

• Product Name: Benzenesulfonamide, N-(4,4-diphenyl-3-butenyl)-4-methyl-
• CAS NO: 610754-79-5
• Molecular Formula: C23H23NO2S
• Molecular Weight: 377.507
• Mol File: 610754-79-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-(4,4-diphenyl-3-butenyl)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(4,4-diphenyl-3-butenyl)-4-methyl-(610754-79-5)
• EPA Substance Registry System: Benzenesulfonamide, N-(4,4-diphenyl-3-butenyl)-4-methyl-(610754-79-5)

Safety Data

• Hazardous Substances Data: 610754-79-5(Hazardous Substances Data)

Upstream product

• 7632-57-7 diphenylmethylenecyclopropene 
• 70-55-3 toluene-4-sulfonamide 
• 119-61-9 benzophenone 
• 95958-02-4 2-(4,4-diphenylbut-3-en-1-yl)isoindoline-1,3-dione 
• 6078-95-1 4,4-diphenyl-3-butenyl bromide 
• 93007-58-0 4,4-diphenylbut-3-en-1-ylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 5746-94-1 toluene-4-sulfonic acid 4,4-diphenyl-but-3-en-1-yl ester 
• 76694-24-1 4,4-diphenyl-3-buten-1-ol 
• 85375-43-5 4-methyl-N-(4-phenylbut-3-yn-1-yl)benzenesulfonamide 
• 98-80-6 phenylboronic acid 
• 5785-66-0 cyclopropyl diphenyl carbinol 
• 911697-93-3 1-tosyl-[1,3]oxazepan-7-one 
• 1025949-92-1 N-(4-hydroxy-4,4-diphenyl-butyl)-4-methyl-benzenesulfonamide 

Downstream Products

• 93007-58-0 4,4-diphenylbut-3-en-1-ylamine 
• 85375-85-5 N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid 

Relevant articles and documents

Ring-Opening Reactions of MCPs with Sulfonamides Promoted by Metal Triflate Lewis Acids

The reaction of aromatic MCPs with sulfonamides catalyzed by Lewis acids affords the corresponding ring-opened homoallylic sulfonamides in good yields and the reaction of aliphatic MCPs with sulfonamides gives the corresponding pyrrolidine derivatives under the same conditions. Through deuterium-labeling experiments, we found that the reaction process is involved with the rearrangement of a cyclopropylcarbinyl cation and a nonclassic carbonium ion.

Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes

The RhII-catalyzed oxyamination and diamination of alkenes generate 1,2-amino alcohols and 1,2-diamines, respectively, in good to excellent yields and with complete regiocontrol. In the case of diamination, the intramolecular reaction provides

Gold- and silver-catalyzed tandem amination/ring expansion of cyclopropyl methanols with sulfonamides as an expedient route to pyrrolidines

An efficient synthetic route to pyrrolidines that relies on AuCl/ AgOTf-catalyzed tandem amination/ ring expansion of substituted cyclopropyl methanols with sulfonamides is reported herein. The reactions proceed rapidly at 100 °C with catalyst loadings as low as 2 mol % and produce the pyrrolidine products in yields of 30-95%. The method was shown to be applica ble to a broad range of cyclopropyl methanols, including unactivated ones, and sulfonamide substrates containing electron-withdrawing, electron-donating, and sterically-demanding substitu ents. The mechanism is suggested to involve activation of the alcohol substrate by the AuCl/AgOTf catalyst, followed by ionization of the starting material, which causes ring opening of the cyclopropane moiety and trapping by the sulfonamide nucleophile. The resultant aminated acyclic intermediate undergoes subsequent intramolecular hydroamination to give the pyrrolidine.