42091-60-1

Upstream product

• 933-00-6 p-methylbenzenesulfenyl chloride 
• 107-19-7 propargyl alcohol 
• 106-45-6 para-thiocresol 

Downstream Products

• 70411-72-2 1-Methyl-4-(2-methylene-hexane-1-sulfinyl)-benzene 
• 70411-74-4 1-Methyl-4-(3-methyl-2-methylene-butane-1-sulfinyl)-benzene 
• 37616-05-0 1-methyl-4-((2-methylallyl)sulfinyl)benzene 
• 70411-73-3 1-(3,3-Dimethyl-2-methylene-butane-1-sulfinyl)-4-methyl-benzene 
• 70411-75-5 1-methyl-4-[(2-phenyl-2-propenyl)sulfinyl]benzene 
• 5366-49-4 4-toluenesulfonylacetone 
• 16192-08-8 p-tolylsulfonylallene 
• 37616-10-7 2-Methyl-3-(p-toluenesulfinyl)-1-butene 
• 82483-98-5 2-t-butylamino propenyl p-tolyl sulphoxide 

Relevant academic research and scientific papers

Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Br?nsted acids. NMR and DFT study of these cations and their reactions

In strong Br?nsted acids (CF3SO3H, FSO3H, D2SO4), (arysulfonyl)allenes (ArSO2-CR1=C=CR2R3) and (arylsulfinyl)allenes (ArSO-CR1=C=CR2R3) undergo cyclization into the corresponding stable 1,2-oxathiolium ions, which were studied by means of NMR and DFT calculations. Quenching of solutions of these cations with low nucleophilic media, aqueous HCl, leads to their deprotonation with a stereoselective formation of (arysulfonyl)butadienes (for instance, ArSO2-CR1=C-C(Me)=CH2, for R2 = R3 = Me, yields of 87-98%). Reactions of (arysulfonyl)allenes in the system TfOH (0.1 equiv)-HFIP (hexafluoropropan-2-ol) followed by hydrolysis give rise to allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3, yields of 78-99%). Reflux of solutions of (arysulfonyl)allenes in the presence of TfOH (1 equiv) in 1,2-dichlorobenzene leads to the cyclization into thiochromene 1,1-diox-ides in high yields. Under the action of TfOH or AlX3 (X = Cl, Br) followed by hydrolysis of reaction mixtures, (arylsulfinyl)allenes give allyl alcohols (ArSO2-CR1=CH-C(OH)R2R3). Plausible reaction mechanisms have been proposed for all studied reactions.