122471-88-9

Upstream product

• 28995-75-7 (E)-1-((2-iodohex-1-en-1-yl)sulfonyl)-4-methylbenzene 
• 693-02-7 hex-1-yne 
• 34125-84-3 chloromethyl p-tolyl sulfide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 627-19-0 1-Pentyne 
• 139416-65-2 1-Methyl-4-((Z)-2-phenylselanyl-hex-2-ene-1-sulfonyl)-benzene 

Downstream Products

• 105235-59-4 (Z)-2-hexenyl p-tolyl sulfone 

Relevant academic research and scientific papers

Reactions of (E)-2-Iodo-1-tosyl-1-alkenes as Useful Synthetic Intermediates

(E)-2-Iodo-1-tosyl-1-alkenes readily available by iodosulfonization of 1-alkynes were found to be useful synthons for the regio- and/or stereoselective preparation of 1-tosyl-1-alkynes, 1-tosyl-2-alkynes, (Z)-vinyl and (Z)-allyl sulfones, β-tosyl enamines

Regio- and Stereoselective Synthesis of (E)- and (Z)-Allylsulfones from Aldehydes and Alkynes

Several (E)- and (Z)-1-p-toluenesulfonyl(=tosyl)-2-alkenes, allylsulfones, were regio- and stereoselectively prepared from aldehydes and alkynes, respectively, in good yields by application of the results of our previous investigation on "syn-effect" and

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.