Photo-Rearrangements in a Micellar Environment

  • A. K. Singh
  • T. S. Raghuraman
  • P. Deval
  • S. Lalitha

Abstract

Aryl esters and amides, solubilized in aqueous SDS, underwent rearrangement on photolysis giving ortho and para migration products. Only one of the possible ortho isomers, whenever two isomeric products are possible, is obtained in preference to the para isomer. Cage and polarity effects were attributed to this selectivity. SDS solubilized ionyl compounds also showed selectivity in their photoreactions. Thus, while a major reaction of lower homologues such as B-ionyl compounds was found to be 1,5 sigmatropic H-migration, longer homologues such as retinal exhibited cis, transphotoisomerization only. The polarity of micellar interface has been suggested to be responsible for the observed data.

Keywords

Surfactant Migration Cage Recombination Amide 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J.K. Thomas, Chem. Rev., 80, 283 (1980) and references cited therein.Google Scholar
  2. 2.
    N.J. Turro, M. Gratzel and A.M. Braun, Angew. Chem. Int. Ed. Engl., 19675 (1980) and references cited therein.Google Scholar
  3. 3.
    D. Bellus, Adv. Photochem., 8, 109 (1971).CrossRefGoogle Scholar
  4. 4.
    M.M. Abdel-Malik and P. de Mayo, Can. J. Chem., 62, 1275 (1984) and references cited therein.Google Scholar
  5. 5.
    R. Chenevert and N. Voyer, Tetrahedron Lett., 5007, (1984) and references cited therein.Google Scholar
  6. 6.
    V.T. Ramakrishna and J. Kagan, J. Org. Chem., 35, 290 (1970).Google Scholar
  7. 7.
    D.A. Plank, Tetrahedron Lett., 5423, (19 68).Google Scholar
  8. 8.
    M. Ottolenghi, Adv. Photochem., 12, 97 (1980).CrossRefGoogle Scholar
  9. 9.
    R.S.H. Liu and A. E. Asato, Tetrahedron, 40, 1931 (1984) and references cited therein.Google Scholar
  10. 10.
    L. Salem, Pure Appl. Chem., 33, 317 (1973).CrossRefGoogle Scholar
  11. 11.
    A.I. Vogel, “A Text-book of Practical Organic Chemistry”. 3rd Edn., ELBS/Longman, London, 1971.Google Scholar
  12. 12.
    R.C. Weast and M. Astle, “CRC Handbook of Chemistry and Physics”, CRC Press, Boca Raton, 61 Edn., 1980–81.Google Scholar

Copyright information

© Plenum Press, New York 1989

Authors and Affiliations

  • A. K. Singh
    • 1
  • T. S. Raghuraman
    • 1
  • P. Deval
    • 1
  • S. Lalitha
  1. 1.Department of ChemistryIndian Institute of TechnologyBombayIndia

Personalised recommendations