Structural Features of Certain p‐substituted Phenyl 2‐nitrovinyl Sulfones |
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Authors: | Dilyana Zvezdova Stoyanka Stoeva Dimitar Aleksiev |
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Affiliation: | 1. Department of Organic Chemistry, Bourgas Assen Zlatarov University, 8010 Bourgas, Bulgaria;2. Laboratory of Mathematical Chemistry, Bourgas Assen Zlatarov University, 8010 Bourgas, Bulgaria |
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Abstract: | 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. |
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Keywords: | Sulfinate S‐vinylation Phenyl 2‐nitrovinyl sulfones Nucleophilic vinylic substitution Substituent effects E‐isomers |
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