3147-37-3

Upstream product

• 29281-83-2 4-methylbenzensulphonamide potassium salt 
• 51953-62-9 N-[Bis-(4-dimethylamino-phenyl)-methylene]-4-methyl-benzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 90-94-8 bis(p-dimethylaminophenyl)methanone 

Downstream Products

• 1220284-22-9 (S)-2-(bis(4-(dimethylamino)phenyl)methyl)cyclohexanone 
• 1262969-10-7 (R)-2-(bis(4-(dimethylamino)phenyl)methyl)cyclohexanone 

Relevant academic research and scientific papers

Catalytic asymmetric α-alkylation of ketones and aldehydes with N-benzylic sulfonamides through carbon-nitrogen bond cleavage

A range of ketones and aldehydes smoothly undergo asymmetric SN1 α-alkylation with N-benzylic sulfonamides in the presence of 10 mol % of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent

Nucleophilic reactivities of imide and amide anions

(Figure presented) The kinetics of the reactions of amide and imide anions 2a-o with benzhydrylium ions 1a-i and structurally related quinone methides 1j-q have been studied by UV-vis spectroscopy in DMSO and acetonitrile solution. The second-order rate constants (log k2) correlated linearly with the electrophilicity parameters E of 1a-q according to the correlation log k 2 = s(N + E) (Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957), allowing us to determine the nucleophilicity parameters N and the nucleophile-specific parameters s for these nucleophiles. The reactivities of all sulfonamide and diacylimide anions are found in a relatively small range (15 aH. These effects can be attributed to the absence of resonance stabilization of one of the lone pairs in the amide or imide anions. As amide and imide anions are exclusively attacked at nitrogen by benzhydrylium ions, Kornblums interpretation of the ambident reactivity of amide anions has to be revised.