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

Article abstract of DOI:10.1021/ja00211a035

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