35925-44-1

Upstream product

• 824-79-3 sodium 4-methylbenzenesulfinate 
• 106-96-7 propargyl bromide 
• 16192-08-8 p-tolylsulfonylallene 
• 149035-06-3 (S₅,S_S)-5-ethoxy-3-(p-tolylsulfinyl)furan-2(5H)-one 
• 10449-66-8 5-methoxyfuran-2(5H)-one 
• 106-45-6 para-thiocresol 
• 16192-07-7 4-tosylacetonitrile 
• 97479-48-6 3-p-tolylsulphonyl-2-p-tolylthiopropene 
• 463-49-0 1,2-propanediene 
• 1950-78-3 p-toluenesulfonyl iodide 

Downstream Products

• 115524-58-8 p-tolyl 3-p-tolylsulfonylprop-1-enyl sulfone 
• 129222-58-8 4-acetoxy-2,5-bis(4-methylphenylsulfonyl)-1-pentene 

Relevant academic research and scientific papers

Reactions of propargylic bromides with sodium sulfinates

A one-pot, palladium-catalyzed synthesis of substituted 2,3-bissulfonylpropenes starting with propargylic bromides and sodium sulfinates (RSO2Na) in the presence of n-Bu4NF under refluxing aqueous 1,4-dioxane conditions for eight hours in moderate yields is described. Georg Thieme Verlag Stuttgart. New York.

Abnormal behaviour of allenylsulfones under Lu's reaction conditions: Synthesis of enantiopure polyfunctionalised cyclopentenes

Formal [3+2] cycloadditions of 5-alkoxyfuran-2(5H)-ones 1 and 2 with allenylsulfones 3-5, promoted by different nucleophiles, afford 3-alkoxy5-arylsulfonyl-3,3 a,6,6 a-tetrahydro-1Hcyclopenta[c]furan-l-ones in good yields with complete control of both regio- and π-facial selectivity. The incorporation of a sulfinyl group on the furanone ring enhances the reactivity of the furanones and allows the synthesis of optically pure, bicyclic adducts in good yields. Allenylsulfones evolve through a different mechanism to that proposed for allenoates (Lu's reaction) and afford bicyclic adducts in which the sulfonyl group is joined to C-5. This has advantages on the stereochemical control of further reactions leading to enantiomerically pure polyfunctionalised cyclopentenes and cyclopentanes.

Free radical addition reactions of allylic sulfones to alkenes

Intermolecular radical reactions involving formal addition of the sulfonyl and allyl fragments of an allylic sulfone across the double bond of an alkene are described. Reactions are most successful when the allylic sulfone has an electron withdrawing group at the 2-position. Only monosubstituted alkenes give useful yields of adducts, though both electron withdrawing and electron donating substituents are effective.