1072-25-9

Upstream product

• 4282-40-0 1-Iodoheptane 
• 463-49-0 1,2-propanediene 
• 122471-78-7 1-Methyl-4-((Z)-2-phenylselanyl-dec-2-ene-1-sulfonyl)-benzene 
• 13125-66-1 n-heptylmagnesium bromide 
• 106-96-7 propargyl bromide 

Downstream Products

• 109239-64-7 2-((Z)-2-Phenyl-dec-2-enyl)-malonic acid diethyl ester 
• 109239-65-8 2-((Z)-2-Phenyl-dec-2-enyl)-malonic acid diethyl ester 
• 111223-41-7 diethyl 2-<(E)-2-(1'-propenyl)-2-decenyl> propanedioate 
• 111223-42-8 diethyl 2-<(Z)-2-(1'-propenyl)-2-decenyl> propanedioate 
• 119841-11-1 2-[1-((E)-1-Methylene-3-trimethylsilanyl-allyl)-octyl]-malonic acid dimethyl ester 
• 119841-10-0 2-[(Z)-2-((E)-2-Trimethylsilanyl-vinyl)-dec-2-enyl]-malonic acid dimethyl ester 
• 119841-09-7 2-[(Z)-2-((E)-2-Trimethylsilanyl-vinyl)-dec-2-enyl]-malonic acid dimethyl ester 
• 111223-51-9 methyl 4-isopropenyl-2-phenylsulfonyl-4-dodecenoate (E isomer) 
• 111223-52-0 methyl 4-isopropenyl-2-phenylsulfonyl-4-dodecenoate (Z isomer) 
• 126385-60-2 (Z)-2-(Benzhydrylidene-amino)-4-isopropenyl-dodec-4-enoic acid methyl ester 
• 119472-68-3 2-((E)-2-Cyclohex-1-enyl-dec-2-enyl)-malonic acid dimethyl ester 
• 119472-69-4 2-((Z)-2-Cyclohex-1-enyl-dec-2-enyl)-malonic acid dimethyl ester 
• 119472-71-8 2-[(E)-2-(4-Methyl-cyclohex-1-enyl)-dec-2-enyl]-malonic acid dimethyl ester 
• 119472-72-9 2-[(Z)-2-(4-Methyl-cyclohex-1-enyl)-dec-2-enyl]-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Conversion of alkyl- and arylallenes into 1-alkynes through metallated intermediates

A number of acetylenes RCH2C≡CH have been obtained by metallation of the allenes RCH=C=CH2 or mixtures of acetylenes and allenes with n-BuLi in THF-hexane and hydrolysis after allowing the metallated allenes to rearrange at roam temperature or by heating under reflux.

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.

AN EFFICIENT COUPLING REACTION OF ANIONIC PROPARGYL AND ORGANIC HALIDES

The organometallic produced by controlled lithiation of allene functions as an efficient propargylic anion equivalent in coupling reactions with alkyl and allyl halides.