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Russian Journal of Organic Chemistry

, Volume 55, Issue 6, pp 792–795 | Cite as

Reactivity of 2-Sulfobenzoic Acid Imide and Benzenesulfonamide in Arenesulfonylation

  • T. P. KustovaEmail author
  • M. A. Agafonov
  • A. A. Kruglyakova
  • L. B. Kochetova
Article
  • 11 Downloads

Abstract

Experimental study of the kinetics of the reactions of 2-sulfobenzoic acid imide (saccharin) and benzenesulfonamide with 3-nitrobenzenesulfonyl chloride in a 1,4-dioxane-water mixture (80:20 by weight) in the temperature range 298–318 K has shown that both compounds are low reactive (k298 = 1.66 × 10−4 and 3.37 × 10−3 L mol−1 s−1, respectively). The activation barriers to these reactions exceed 50 kJ/mol. Aqueous dioxane can be recommended as a solvent for the preparation of N-(benzenesulfonyl)-3-nitrobenzenesulfonamide in up to 87% yield.

Keywords

kinetics arenesulfonylation 2-sulfobenzoic acid imide benzenesulfonamide 3-nitrobenzenesulfonyl chloride 1,4-dioxane 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • T. P. Kustova
    • 1
    Email author
  • M. A. Agafonov
    • 1
  • A. A. Kruglyakova
    • 1
  • L. B. Kochetova
    • 1
  1. 1.Ivanovo State UniversityIvanovoRussia

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