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4-Phenylsulfonyl-2,3,5,6-tetrachloropyridine: synthesis and synthetic utility

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Abstract

4-Phenylsulfonyl-2,3,5,6-tetrachloropyridine was synthesized from the reaction of sodium phenylsulfinate with pentachloropyridine in optimized reaction condition. The reaction of some mono- and bidentate N and O nucleophiles with 4-phenylsulfonyl-2,3,5,6-tetrachloropyridine was studied in order to assess the impact of electron-withdrawing functional group (PhSO2−) upon regiochemistry of aromatic nucleophilic substitution. Substitution generally occurs at 4-position of pyridine ring, by less steric hindrance nucleophiles although mixtures of products (ortho- and para-substituted) are obtained with more steric hindrance cases. The structures of all the compounds were confirmed by IR, 1H NMR and 13C NMR spectroscopy as well as elemental analysis and X-ray crystallography.

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Acknowledgements

The authors wish to thank Vali-e-Asr University of Rafsanjan for partially funding this work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan, 77176, Islamic Republic of Iran

    Reza Ranjbar-Karimi & Alireza Poorfreidoni

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  1. Reza Ranjbar-Karimi
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  2. Alireza Poorfreidoni
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Correspondence to Reza Ranjbar-Karimi.

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Ranjbar-Karimi, R., Poorfreidoni, A. 4-Phenylsulfonyl-2,3,5,6-tetrachloropyridine: synthesis and synthetic utility. J IRAN CHEM SOC 14, 933–941 (2017). https://doi.org/10.1007/s13738-016-1043-3

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  • DOI: https://doi.org/10.1007/s13738-016-1043-3

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