80641-22-1

Upstream product

• 80641-24-3 Methyl β-Hydroxy-α-cyano-p-nitrocinnamate 
• 112220-58-3 (Z)-2-Cyano-3-hydroxy-3-(4-nitro-phenyl)-acrylic acid methyl ester 
• 80641-23-2 methyl (Z)-β-chloro-α-cyano-p-nitrocinnamate 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 80641-32-3 Methyl α-Cyano-β-methoxy-β-(p-nitroanilino)acrylate 
• 80641-30-1 Methyl (E)-α-Cyano-β-(p-methylphenoxy)-p-nitrocinnamate 
• 80641-31-2 Methyl (Z)-α-Cyano-β-(p-methylphenoxy)-p-nitrocinnamate 
• 80641-29-8 2-Cyano-3,3-dimethoxy-3-(4-nitro-phenyl)-propionic acid methyl ester 
• 80641-27-6 Methyl (E)-α-Cyano-β-methoxy-p-nitrocinnamate 
• 80641-28-7 Methyl (Z)-α-Cyano-β-methoxy-p-nitrocinnamate 
• 112220-57-2 Sodium; (Z)-2-cyano-2-methoxycarbonyl-1-(4-nitro-phenyl)-ethenolate 
• 80641-23-2 methyl (Z)-β-chloro-α-cyano-p-nitrocinnamate 
• 80641-26-5 Methyl (Z)-α-Cyano-p-nitro-β-(p-tolylthio)cinnamate 

Relevant academic research and scientific papers

Stereochemistry of Substitution of Good Nucleofuges at the Stereoconvergence Region as a Tool for Investigating the Rapid Step of Nucleophilic Vinylic Substitution

Methyl-α-cyano-β-X-p-nitrocinnamates (5; X=Cl, Br, OTs, OTf) were prepared.The five (E) isomers and the (Z) isomers (X=Cl, Br, OMs) were separated and their structures assigned.Substitution of the eight substrates by p-MeC6H4S-M+ and

Chloride Ion Exchange and E Z Isomerization of an Electrophilic Vinyl Chloride

The exchange (ex) and the accompanying isomerization (isom) in the reaction of methyl (E)- and (Z)-β-chloro-α-cyano-p-nitrocinnamates with 36Cl- in acetonitrile were investigated.Exchange was much faster than isomerization, kex/kisom = 54 and 123 .Both exchange and isomerization were faster for (Z)-5 than (E)-5.The exchange was a relatively fast process, and extrapolation suggested that kex(Cl-)/ksubstitution(piperidine) of 5 is 2.7.The results are discussed in terms of formation of intermediate carbanion, which exchanged the chloride with highly preferred retention.The modes of rotations leading to inversion (isomerization) were analyzed, and it was shown that isomerizations via 120 deg counterclockwise rotation and 180 deg clockwise rotation around the Cα-Cβ bond in the carbanion are distinguishable in principle, although we failed to determine the mode of rotation in our system.The relatively high nucleophilicity of Cl- was ascribed to lower hidden reversal of the nucleophilic attack by Cl- than in less activated systems.The differences in reactivity of (Z)-5 and (E)-5 were analyzed in terms of steric interactions in the transition states for the 60 deg and 120 deg internal rotations.

Nucleophilic Attacks on Carbon-Carbon Double Bonds. 28.1,2 Complete and Partial Stereoconversion in the Substitution of Methyl (E)- and (Z)-β-Chloro-α-cyano-p-nitrocinnamates by Nucleophiles

Methyl (E)- and (Z)-β-chloro-α-cyano-p-nitrocinnamates 5-E and 5-Z were prepared and separated.The stereochemistry of the substitution of the chlorine by nucleophiles was invastigated in MeCN, MeOH, or their mixtures.Reaction with p-toluenethiolate ion ga