133497-27-5

Upstream product

• 97821-21-1 isopropyl N-phenyl sulfinamoyl ester 
• 31562-43-3 tert-butylsulfinyl chloride 
• 62-53-3 aniline 
• 108-86-1 bromobenzene 
• 146374-27-8 S-tert-butylsulfinimide 
• 2211-92-9 di-tert-butyl sulfoxide 

Downstream Products

• 133497-29-7 2,6-bis(1,1-dimethylethyl)-4,4,8,8-tetramethyl-3,7-diphenyl-1,5,2λ(4),6λ(4),3,7,4λ(4),8λ(4)-dioxadithiadiazadialumocan 
• 133497-32-2 2,6-bis(1,1-dimethylethyl)-3,7-diphenyl-4,4,8,8-tetrakis{(trimethylsilyl)methyl}-1,5,2λ(4),6λ(4),3,7,4λ(4),8λ(4)-dioxadithiadiazadiindocan 
• 29099-08-9 2-methylpropane-2-sulfinic acid 
• 62-53-3 aniline 
• 97821-21-1 isopropyl N-phenyl sulfinamoyl ester 
• 1372133-65-7 (S)-2-methyl-N-phenylpropane-2-sulfinamide 
• 1372133-79-3 (R)-N-allyl-N-phenyl tert-butanesulfinamide 

Relevant academic research and scientific papers

Kinetic Resolution of Sulfinamides via Asymmetric N-Allylic Alkylation

An efficient kinetic resolution of sulfinamides via an asymmetric N-allylic alkylation reaction was realized using hydroquinine as a catalyst under mild conditions. The kinetic resolution of a range of Morita-Baylis-Hillman adducts and N-aryl tert-butylsulfinamides was highly effective. In addition, the synthetic utility of the protocol was demonstrated by a scaled-up reaction. Density functional theory calculations provide convincing evidence for the interpretation of stereoselection.

Sulfonimidates: Useful Synthetic Intermediates for Sulfoximine Synthesis via C-S Bond Formation

Medicinally relevant sulfoximines are accessed from C-S coupling of sulfonimidates and commercially available organomagnesium reagents. Sulfonimidates are conveniently synthesized by oxidative alkoxylation of readily available sulfinamides. This constitutes a general C-S coupling approach for the synthesis of sulfoximines.

Tert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds

Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions and then subsequently treated with a variety of nitrogen, carbon, or oxygen nucleophiles to afford a wide range of the corresponding sulfinic acid amides, new sulfoxides, and sulfinic acid esters.

Palladium-catalyzed C-N cross coupling of sulfinamides and aryl halides

The palladium-catalyzed C-N cross coupling of sulfinamides and aryl halides is reported. In the presence of Pd2(dba)3, tBuXPhos, NaOH, and a small amount of water, the C-N cross coupling of chiral tert-butanesulfinamide and aryl halides was accomplished to give N-aryl tert-butanesulfinamide without racemization, and the coupling of racemic p-toluenesulfinamide smoothly afforded N-aryl p-toluenesulfinamides. 2-Bromopyridine was also suitable for the coupling. Addition of a small amount of water to the catalytic system was of importance to obtain high yields.

Hydrolysis of N-phenylalkanesulfinamides in aqueous mineral acids

The acid-catalyzed hydrolysis of N-phenylalkanesulfinamides (RSONHPh; 1, R = iPr; 2, R = tBu; 3, R = 1-adamantyl) has been studied in aqueous mineral acids. Hydrolysis was found to proceed via a slow spontaneous (uncatalyzed) pathway, an A-2 (bimolecular) acid-catalysis pathway, and an acid-dependent nucleophilic catalysis pathway, the last of which predominates in hydrobromic and hydrochloric acid solutions. A mechanistic switch over from A-2 to A-1 was detected for compounds 2 and 3 in concentrated sulfuric acid. Order of catalytic activity, effect of added salts, Arrhenius parameters, kinetic solvent isotope, and solvent effects are all consistent with the proposed mechanisms. Copyright Taylor & Francis Group, LLC.