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Russian Chemical Bulletin

, Volume 55, Issue 2, pp 312–316 | Cite as

Reactions of aminophenols with formaldehyde and hydrogen sulfide

  • V. R. Akhmetova
  • G. R. Nadyrgulova
  • S. R. Khafizova
  • T. V. Tyumkina
  • A. A. Yakovenko
  • M. Yu. Antipin
  • L. M. Khalilov
  • R. V. Kunakova
  • U. M. Dzhemileva
Article

Abstract

The reaction of m-aminophenol with CH2O and H2S (1: 2: 1 ratio) afforded 2, 12-dioxa-4, 14-dithia-6, 16-diazatricyclo[15.3.1.17,11]docosa-1(20), 7(22), 8, 10, 17(21), 18-hexaene in ∼9% yield. Aminophenol o-and p-isomers react with CH2O and H2S (1: 3: 2) to form 2-and 4-[4H-1,3,5-dithiazin-5(6H)-yl]phenols in 86 and 71% yields, respectively. In the crystal structure of the latter, molecules contain dithiazine cycles in the chair conformation with the axial hydroxyphenyl group. Molecular packing represents a combination of molecules forming chains due to the OH...S intermolecular hydrogen bond.

Key words

thiomethylation o-, m-, and p-aminophenols formaldehyde hydrogen sulfide X-ray diffraction analysis 

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • V. R. Akhmetova
    • 1
  • G. R. Nadyrgulova
    • 1
    • 2
  • S. R. Khafizova
    • 1
  • T. V. Tyumkina
    • 1
  • A. A. Yakovenko
    • 3
  • M. Yu. Antipin
    • 3
  • L. M. Khalilov
    • 1
  • R. V. Kunakova
    • 2
  • U. M. Dzhemileva
    • 1
  1. 1.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfaRussian Federation
  2. 2.Ufa State Institute of ServiceUfaRussian Federation
  3. 3.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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