61783-61-7

Upstream product

• 112389-72-7 1-((E)-3-Chloro-2-phenylselanyl-prop-1-ene-1-sulfonyl)-4-methyl-benzene 
• 74-88-4 methyl iodide 
• 98-59-9 p-toluenesulfonyl chloride 
• 1114903-76-2 but-2-yn-1-yl 4-methylbenzenesulfinate 
• 112389-71-6 1-Methyl-4-((E)-2-phenylselanyl-prop-1-ene-1-sulfonyl)-benzene 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 122471-89-0 1-Methyl-4-(3-phenylselanyl-but-3-ene-2-sulfonyl)-benzene 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 

Downstream Products

• 1233250-63-9 (3S,3aR,6aS,SS)-3-ethoxy-4-methyl-6a-[(4-methylphenyl)sulfinyl]-5-[(4-methylphenyl)sulfonyl]-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one 
• 72157-40-5 (2R)-2r,3,4c-trimethyl-5c-phenyl-2-[(S)-1-(toluene-4-sulfonyl)-ethyl]-oxazolidine 

Relevant academic research and scientific papers

Metal-Free C-C Coupling of an Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated in Situ Generation of Sulfinate Anion

Vinyl sulfones are privileged motifs known for their biological activity and synthetic utility. Synthetic transformations to efficiently access high-value compounds with these motifs are desired and sought after. Herein, a new procedure is described to fo

Silver-catalyzed rearrangement of propargylic sulfinates to allenic sulfones

Treatment of propargylic sulfinate esters with 2 mol% of silver hexafluoroantimonate results in the rapid formation of allenic sulfones in essentially quantitative yield.

Preparation of Allenic Sulfones and Allenes from the Selenosulfonation of Acetylenes

β-(Phenylseleno)vinyl sulfones 2 are readily obtained from the free-radical selenosulfonation of acetylenes.Compounds 2 isomerize to allyl sulfones 4 under base-catalyzed conditions in nearly quantitative yield, with high stereoselectivity favoring the Z configuration.Allyl sulfones 4 afford generally high yields of allenic sulfones 1 when subjected to oxidation with m-chloroperbenzoic acid or tert-butyl hydroperoxide, followed by selenoxide syn-elimination.The sulfone-stabilized anion intermediates in the isomerizations of 2 to 4 can be alkylated, deuterated,or silylated in the α-position prior to oxidation, providing allenic sulfones with an additional α-substituent.In some cases, spontaneous elimination of the phenylseleno group occurred, producing the allenic sulfone without the need for an oxidation step.Desulfonylation of allyl sulfones 4f, 4c, and 25 with sodium amalgam afforded vinyl selenides that were converted to allenes in moderate to good yields by oxidation-elimination.The copper catalyzed coupling of allyl sulfones 4 with Grignard reagents comprises an alternative route to vinyl selenide precursors of allenes.These procedures permit the synthesis of various α- and γ-substituted allenic sulfones and allenes from acetylenes.

A GENERAL SYNTHESIS OF ALLENIC SULFONES FROM ACETYLENES USING SELENOSULFONATION

Terminal acetylenes were converted to 1- and 3-substituted allenic sulfones via selenosulfonation, deprotonation, alkylation and selenoxide elimination.