5331-33-9

Upstream product

• 76937-39-8 threo-dimethyl α-fluoro-α'-chlorosuccinate 
• 563-79-1 2,3-Dimethyl-2-butene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 56218-62-3 2-(4-methylphenylsulfonamido)acetyl chloride 
• 74427-60-4 1-(phenylsulphonylamino)acetyl chloride 

Downstream Products

• 118657-84-4 r-1,t-3-bis(methoxycarbonyl)-1-chloro-t-2-methyl-c-2-phenylcyclopropane 
• 118657-83-3 3-chloro-r-3,t-4-bis(methoxycarbonyl)-c-5-methyl-t-5-phenyl-1-pyrazoline 
• 31419-01-9 dimethyl 3,3-diphenyl-3H-pyrazole-4,5-dicarboxylate 
• 118657-85-5 trans-1,3-bis(methoxycarbonyl)-1-chloro-2,2-diphenylcyclopropane 
• 118657-84-4 1-chloro-r-1,t-3-bis(methoxycarbonyl)-c-2-methyl-t-2-phenylcyclopropane 

Relevant academic research and scientific papers

A Simple Approach to the Synthesis of 1,4-Bis(arylsulfonyl) tetrahydropyrazine-2,5-diones

The addition of triphenylphosphine to dimethyl acetylenedicarboxylate in the presence of arylsulfonylglycyl chlorides leads to 1,4-bis-arylsulfonyl- tetrahydropyrazine-2,5-diones and dimethyl (E)-2-chloro-2-butenedioate.

REACTIONS OF CHLORINE MONOFLUORIDE. IV. ADDITION OF CHLORINE MONOFLUORIDE TO HALOGEN-SUBSTITUTED ALKENES

The reactions of chlorine monofluoride with halogenoethylenes (1,1-dichloro-, 1,2-dichloro-, trichloro-, and tetrachloroethylenes) and halogenopropenes ( 3-bromo-, 3,3,3-trichloro-, E- and Z-1,3-dichloro-, 3-chloro-2-methyl-, and perfluoropropenes) were investigated in inert solvents in the presence of ethyl acetate as external nucleophile.In all cases chloroacyloxy adducts were isolated and identified in addition to the chlorofluorination products, and this indicates an electrophilic mechanism for the chlorofluorination of polyhalogenoalkenes.Methyl chloromaleate, chlorofumarate, chlorofluoroethylenedicarboxylate, α,β-difluoroacrylate, and perfluoromethacrylate in anhydrous hydrogen fluoride form the corresponding chlorofluoro adducts with satisfactory yields, whereas the reaction takes place with difficulty in inert solvents.

APPLICATIONS OF THE ENE REACTION. SYNTHESIS AND PROPPERTIES OF SUBSTITUTED &α-METHYLENE-&γ-LACTONES

Substituted dimethyl 1,4-pentadiene-1,2-dicarboxylates ( 1 or 3 ) may be prepared by AlCl3-promoted or thermal ene reaction of olefins with dimethyl acetylenedicarboxylate.Lactonization of these adducts is catalyzed by acid.In the presence of 80 percent H2SO4 the predominant product ( ca. 80 percent ) is a (Z)-dihydro-3-carbomethoxymethylene-2(3H)-furanone ( 2 or 4 ).Cyclization with anhydrous HCl affords a mixture of products the composition of which depends on the starting material; major products include the corresponding (E)- and γ-lactone isomers ( 6 and 7 ).Detailed 1H and 13C nmr are reported for all compounds.The structures of the (E)-4,5,5-trimethyl-, (Z)-4,5,5-trimethyl-, and (Z)-4,4,5,5-tetramethyl furanone derivatives ( 6a, 2a, and, 2b,) have been established by X-ray crystallography.The properties of some of these lactones are discussed, as are possible methods of removal of the carbomethoxyl from 2.