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

doi:10.1007/s13738-016-1043-3

Paper

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

Published Apr 1, 2017 · R. Ranjbar‐Karimi, Alireza Poorfreidoni

Journal of the Iranian Chemical Society

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Abstract

Abstract4-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 (PhSO_2−) 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.Graphical Abstract

Study Snapshot

4-Phenylsulfonyl-2,3,5,6-tetrachloropyridine is a useful synthetic intermediate for evaluating the impact of electron-withdrawing functional groups on aromatic nucleophilic substitution regiochemistry.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

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

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Citations