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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 5
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Original Articles

A Facile and Convenient Synthesis of Lipophilic Tetraalkylammonium or Phosphonium Hydrogen Sulfates

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Pages 521-533 | Published online: 05 Dec 2006

References

  • Brändström , A. 1974 . “Preparative Ion Pair Extraction: An Introduction to Theory and Practice” , Stockholm : Apotekarsocieten/Hässle Lakemedel .
  • Starks , C. M. and Liotta , C. 1978 . “Phase-Transfer Catalysis: Principles and Techniques” , New York : Academic Press .
  • Dehmlow , E. V. and Dehrnlow , S. S. 1983 . “Phase-Transfer Catalysis”, , 2nd Ed. , Weinheim/Bergstr, , Germany : Verlag-Chemie .
  • Dehmlow , E. V. , Vehre , B. and Brada , V. 1985 . Synthesis , : 508
  • Tetrabutylammonium derivative 2a is, indeed, the only quaternary ammonium hydrogen sulfate commercially available
  • Bar , R. , Sasson , Y. and Blum , J. 1983 . Reactive Polymers , 1 : 315
  • Reaction must be carried out in an efficient fume hood due to the poisonous character of HN3. Moreover care should be paid owing to the explosive nature of pure HN3.8
  • Andrieth , L. F. and Gibbs , C. F. 1936 . Inorganic Syntheses , 1 : 77
  • A similar excess of KSCN was used also for the synthesis of quaternary ammonium thiocyanates from the corresponding onium bromides.4
  • Ref.1, pag. 81
  • Quaternary methanesulphonates can be used as starting materials for the synthesis of ammonium 12 or phosphonium13 salts with other an ions (e.g. CN−, SCN−, CI−, etc…) via ion-pair extraction (eq. 2).
  • Landni , D. , Maia , A. and Podda , G. 1982 . J. Org. Chem. , 47 : 2264
  • Landini , D. , Maia , A. and Montanari , F. 1978 . J. Am. Chem. Soc. , 100 : 2796
  • Landini , D. , Maia , A. and Montanari , F. 1979 . Nouv. J. Chim. , 3 : 575
  • Williams , H. R. and Mosher , H. S. 1954 . J. Am. Chem. Soc. , 76 : 2984
  • Browne , A. W. 1936 . Inorganic Syntheses , 1 : 79
  • The remaining HN3 was partitioned into organic phase and aqueous phase

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