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

Article abstract of DOI:10.1021/jo00347a003

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