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Structural Features of Certain p ‐substituted Phenyl 2‐nitrovinyl Sulfones
Author(s) -
Zvezdova Dilyana,
Stoeva Stoyanka,
Aleksiev Dimitar
Publication year - 2016
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201500408
Subject(s) - chemistry , intramolecular force , nucleophilic substitution , medicinal chemistry , stereochemistry , substrate (aquarium) , sodium , nucleophile , organic chemistry , catalysis , oceanography , geology
The structure of p ‐substituted phenyl 2‐nitrovinyl sulfones was studied through different spectral methods. It has been found that the nucleophilic substitution reactions of sodium phenylsulfinates with 1‐chloro‐2‐nitroethene occur stereospecifically. The formation of E ‐isomers of this type of substituted phenyl vinyl sulfones was confirmed by FTIR and NMR spectroscopy. It was suggested that the E ‐isomers formation was determined by the more stable conformation of the carbanionic intermediate as a result of intramolecular rotation around single Cα‐Cβ bond. This appears to be the product‐determining pathway during the interaction of sodium phenyl sulfinates with the highly activated substrate 1‐chloro‐2‐nitroethene.