Russian Chemical Bulletin

, Volume 59, Issue 3, pp 560–564 | Cite as

Basic hydrolysis of l,4-bis(triphenylphosphonio)buta-1,3-diene dihalides

  • M. Zh. Ovakimyan
  • A. S. Pogosyan
  • M. L. Movsisyan
  • M. G. Indzhikyan


Basic hydrolysis of 1,4-bis(triphenylphosphonio)buta-1, 3-diene dichloride with 10% NaOH gave isomeric 4-diphenylphosphoryl-4-phenylbut-1(2)-enes and 1-diphenylphosphoryl-1-phe-nylbuta-1, 3-diene, the products of anionotropic migration of a phenyl group from the P atom to the α-position. Hydrolysis with Na2CO3 afforded only the diene product. In both cases, triphe-nylphosphine and triphenylphosphine oxide were isolated as secondary products. Dehydro-chlorination of 2-chloro-1,4-bis(triphenylphosphonio)but-2-ene dibromide with triphenylphosphine was proposed as a new convenient route to 1,4-bis(triphenylphosphonio)buta-1,3-diene dibromide.

Key words basic hydrolysis anionotropic rearrangements phosphonium salts dienes l,4-bis(triphenylphosphonio)buta-1,3-diene dihalides phosphine oxid 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    F. Plenat, A. Bennamara, L. Chiche, H. Christau, Phosphorus Sulfur, 1986, 26, 39.CrossRefGoogle Scholar
  2. 2.
    C. Ivancsics, E. Zbiral, Monatsh. Chem., 1975, 106, 839.CrossRefGoogle Scholar
  3. 3.
    E. Zbiral, E. Werner, Ann. Chem., 1967, 707, 130.Google Scholar
  4. 4.
    J. Brophy, K. Freeman, M. Gallagher, J. Chem. Soc. 1968, 2761.Google Scholar
  5. 5.
    H. Christol, J. Joubert, M. Soleiman, C.R. Acad. Sci. Paris, 1974, 279, 167.Google Scholar
  6. 6.
    H. Christau, F. Plenat, F. Guida-Petrasanta, Phosphorus Sulfur, 1987, 34, 75.CrossRefGoogle Scholar
  7. 7.
    J. Brophy, M. Gallagher, Aust. Chem. J., 1969, 22, 1385.CrossRefGoogle Scholar
  8. 8.
    M. Zh. Ovakimyan, S. K. Barsegyan, N. M. Kikoyan, M. G. Indzhikyan, Zh. Obshch. Khim., 2005, 75, 164 [Russ. J. Gen. Chem. (Engl. Transl.), 2005, 75].Google Scholar
  9. 9.
    H. Christau, L. Chiche, F. Plenat, Tetrahedron, 1985, 13, 2717.CrossRefGoogle Scholar
  10. 10.
    H. Christau, G. Duc, H. Christol, Synthesis, 1983, 5, 374.CrossRefGoogle Scholar
  11. 11.
    M._Zh. Ovakimyan, S. K. Barsegyan, M. L. Movsisyan, G. A. Panosyan, M. G. Indzhikyan, Zh. Obshch. Khim., 2008, 78, 2052 [Russ. J. Gen. Chem. (Engl. Transl.), 2008, 78].Google Scholar

Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • M. Zh. Ovakimyan
    • 1
  • A. S. Pogosyan
    • 1
  • M. L. Movsisyan
    • 1
  • M. G. Indzhikyan
    • 1
  1. 1.Institute of Organic Chemistry, Scientific and Technological Center of Organic and Pharmaceutical ChemistryNational Academy of Sciences of the Republic of ArmeniaYerevanRepublic of Armenia

Personalised recommendations