Inclusion of α-phenyl-N-p-methylphenyl Nitrone in β- Cyclodextrin: Formation of 1G : 1H and 1G : 2H Complexes and the Remarkably Fast 1,3-Dipolar Cycloaddition of the 1G : 2H Complex with Olefins in the Solid State

  • V. Ramamoorthy
  • A. Ramasubbu
  • S. Muthusubramanian
  • S. Sivasubramanian

Abstract

The nitrone is found to be included in the β-cyclodextrin cavity in two different stoichiometries viz., 1G : 1H and 1G : 2H – the existence of which is proved by physical methods. The 1G : 2H complex of the nitrone serves as a good potent dipolarophile in the 1,3-dipolar cycloaddition reactions with olefins resulting in rate acceleration and regioselection.

α-phenyl-N-p-methylphenylnitrone β-Cyclodextrin-Nitrone complexes [1G : 1H and 1G : 2H] 1,3-dipolar Cycloaddition reactions rate acceleration regioselectivity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J.L. Atwood, J.E.D. Davies and D.D. MacNicol, (eds.): Inclusion Compounds, Academic Press, London, Vol. 1–3 (1984).Google Scholar
  2. 2.
    J. Szejtli: Cyclodextrins and Their Inclusion Complexes, Akademiai Kiado, Budapest (1982).Google Scholar
  3. 3.
    M.L. Bender and M. Komiyama: Cyclodextrin Chemistry; Springer-Verlag; New York (1978).Google Scholar
  4. 4.
    G.F. Sanchez, H.M. Lopez and M.J.C. Gomez: Analyst, 112, 1037 (1987).Google Scholar
  5. 5.
    A. Heredia, G. Requena and G.F. Sanchez: J. Chem. Soc. Chem. Commun. 1814 (1985).Google Scholar
  6. 6.
    J.J. Tufariello and A. Padwa, (eds.): 1,3-Dipolar Cycloaddition Chemistry, Wiley Interscience, New York, Vol. 2, (1986).Google Scholar
  7. 7.
    S. Kanemasa, T. Uemura and E. Wada: Tetrahedron Lett. 33, 7889 (1992).Google Scholar
  8. 8.
    S. Kanemasa, T. Tsuruoka and E. Wada: Tetrahedron Lett. 34, 87 (1992).Google Scholar
  9. 9.
    H.J. Schneider and N.K. Sangwan: Angew. Chem. Intl Ed. Engl. 26, 896 (1987).Google Scholar
  10. 10.
    V. Ramamoorthy, A. Ramasubbu, S. Muthusubramanian and S. Sivasubramanian: Unpublished results.Google Scholar
  11. 11.
    A.I. Vogel: Text book of Practical Organic Chemistry, (5th ed.), ELBS Longman, London (1986).Google Scholar
  12. 12.
    A.G.M. Barrett and G.G. Graboski: Chem. Rev. 86, 751 (1986).Google Scholar
  13. 13.
    D.G. Reddy, G. Usha, K.V. Ramanathan and V. Ramamurthy: J. Org. Chem. 51, 3085 (1986).Google Scholar
  14. 14.
    H.A. Benesi and J.H. Hildebrand: J. Am. Chem. Soc. 71, 2703 (1949).Google Scholar
  15. 15.
    W. Saenger: Angew. Chem. Intl. Ed. Engl. 19, 344 (1980).Google Scholar
  16. 16.
    P.V. Demarco and A.L. Thakkar: J. Chem. Soc. Chem. Commun. 2 (1970).Google Scholar
  17. 17.
    K. Pitchumani, P. Velusamy, S. Sabithamala and C. Srinivasan: Tetrahedron 50, 7903 (1994).Google Scholar
  18. 18.
    K. Pitchumani, P. Velusamy and C. Srinivasan: Tetrahedron 50, 12979 (1994).Google Scholar
  19. 19.
    P. Velusamy, K. Pitchumani and C. Srinivasan: Tetrahedron 52, 3487 (1996).Google Scholar
  20. 20.
    O.L. Alves and S.F. Fanseca: J. Incl. Phenom. 7, 589 (1989).Google Scholar

Copyright information

© Kluwer Academic Publishers 1999

Authors and Affiliations

  • V. Ramamoorthy
    • 1
  • A. Ramasubbu
    • 1
  • S. Muthusubramanian
    • 1
  • S. Sivasubramanian
    • 1
  1. 1.School of Chemistry, Madurai Kamaraj UniversityMaduraiIndia

Personalised recommendations