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Russian Chemical Bulletin

, Volume 56, Issue 5, pp 993–1002 | Cite as

Synthesis of nitro and amino derivatives of benzothiacrown ethers

  • S. N. Dmitrieva
  • N. I. Sidorenko
  • A. I. Vedernikov
  • L. G. Kuz’mina
  • J. A. K. Howard
  • T. M. Buslaeva
  • S. P. Gromov
Article

Abstract

The condensation reaction of 1,2-bis(2-haloethoxy)-4-nitrobenzenes with acyclic α,ω-(oxa)alkanedithiols in the presence of alkali metal carbonates produced a series of nitrobenzodithiacrown ethers with macrocycles of different size. The structures of three ethers were established by X-ray diffraction. A new method was developed for the synthesis of nitrobenzomonothia-15-crown-5 ether. Nitro derivatives of benzodithiacrown ethers were tested as reagents for extraction of palladium(II), platinum(IV), and rhodium(III) from hydrochloric acid solutions. Extraction of PdII salts was found to be highly selective compared to that of PtIV and RhIII salts. Benzodithia-15-crown-5 ether is the most efficient extractant for palladium(II). Reduction of nitrobenzothiacrown ethers with hydrazine hydrate in the presence of a platinum catalyst afforded their amino derivatives.

Key words

1,2-bis(2-haloethoxy)-4-nitrobenzenes α,ω-(oxa)alkanedithiols condensation nitrobenzothiacrown ethers X-ray diffraction study reduction aminobenzothiacrown ethers extraction palladium 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • S. N. Dmitrieva
    • 1
  • N. I. Sidorenko
    • 2
  • A. I. Vedernikov
    • 1
  • L. G. Kuz’mina
    • 3
  • J. A. K. Howard
    • 4
  • T. M. Buslaeva
    • 2
  • S. P. Gromov
    • 1
  1. 1.Photochemistry CenterRussian Academy of SciencesMoscowRussian Federation
  2. 2.M. V. Lomonosov Moscow State Academy of Fine Chemical TechnologyMoscowRussian Federation
  3. 3.N. S. Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussian Federation
  4. 4.Department of ChemistryUniversity of DurhamDurhamUK

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