Skip to main content
SpringerLink
Log in

CIDEP studies of the photolysis of the lignin model compound α-guaiacoxylacetoveratrone: the role of triplet reactions in aqueous and hydroxylic solvents

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Free radical reactions induced by the photolysis of the lignin model compound α-guaiacoxylacetoveratrone have been studied by conventional and time-resolved ESR spectroscopy. In the presence of efficient hydrogen donors such as aqueous and hydroxylic solvents the primary reaction involves photoreduction of the triplet phenacyl ether to form the ketyl radical followed by rapid cleavage to the phenacyl radical and guaiacol. Subsequent formation of polarized guaiacoxyl radicals is due to secondary photo-oxidation. The cleavage of the ketyl radical is retarded in basic media and accelerated in acetic acid. Minor reaction pathways involving excited singlets cannot be ruled out by the current CIDEP observations.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. Castellan, N. Columbo, C. Cucuphat, P. Fornier de Violet, Holzforschung, 43(1989)179.

    Article  CAS  Google Scholar 

  2. G. Brunow and B. Eriksson, Acta Chem. Scand. 25(1971)2779.

    Article  CAS  Google Scholar 

  3. J. Gierer and S. Y. Lin, Sven. Papperstidn. 75(1972)233.

    CAS  Google Scholar 

  4. J. A. Schmidt, C. Heitner, G. P. Kelly, and F. Wilkinson, J. Pulp Paper Sci. 161(1990)111.

    Google Scholar 

  5. G. Leary, Nature 217(1968)672.

    Article  CAS  Google Scholar 

  6. S. E. Lebo, W. F. W. Lonsky, T. J. McDonough, and P. J. Medvecz, J. Pulp Paper Sci., 161(1990)139.

    Google Scholar 

  7. G. J. Leary, In The Yellowing of Wood by Light. Part II, Tappi, 51(1968)257.

    CAS  Google Scholar 

  8. C. Vacucci, P. Fornier de Violet, H. Bouas-Lauren, and A. Castellan, J. Photochem. Photobiol. A, 41(1988)251.

    Article  Google Scholar 

  9. W. U. Palm and H. Dreeskamp, J. Photochem. Photobiol. A, 52(1990)439.

    Article  CAS  Google Scholar 

  10. J. A. Schmidt, A. B. Berinstain, F. De Rege, C. Heitner, L. J. Johnston, and J. C. Scaiano, Can. J. Chem. 69(1991)104–107.

    Article  CAS  Google Scholar 

  11. J. C. Scaiano, J. C. Netto-Ferreira, and V. Wintgens, J. Photochem. Photochem A, 59(1991)265.

    CAS  Google Scholar 

  12. M. C. Depew and J. K. S. Wan in S. Patai and Z. Rappopott (Eds.) The Chemistry of the Quinoid Compounds, Part 2, J. Wiley and Sons, 1988, pp. 16; F. J. Adrian, Res. Chem. Intermed. 16(1991)99.

  13. E. Adler, B. O. Lindgren, and U. Saedén, Svensk Papperstidn., 55(1952)245.

    CAS  Google Scholar 

  14. Y. Saburi, K. Minami, Y. Yoshimoto, Nippon Kagaku Zasshi, 88(1967)557.

    CAS  Google Scholar 

  15. J. Gierer and I. Norén, Acta Chem. Scand., 16(1962)1713.

    Article  CAS  Google Scholar 

  16. E. Kam, M. T. Craw, M. C. Depew and J. K. S. Wan, J. Magn. Reson., 57(1986)556.

    Google Scholar 

  17. Pedersen, J. A. (Ed.) In CRC Hanbook of EPR Spectra from Quinones and Quinols, 1983, CRC Press, Boca Raton, Florida, p. 200, and references therein.

    Google Scholar 

  18. D. Leopold, H. Fischer, submitted for publication, 1991.

  19. A. I. Ononye, A. R. McIntosh, and J. R. Bolton, J. Phys. Chem., 90(1986)6266, and references therein; A. I. Ononye and J. R. Bolton, J. Phys. Chem., 90(1986)6270.

    Article  CAS  Google Scholar 

  20. M. Y. Tse, C. Heitner, and J. K. S. Wan, submitted for publication, 1992.

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Queen’s University, K7L 3N6, Kingston, Canada

    J. K. S. Wan, M. Yat Tse & M. Catherine Depew

Authors
  1. J. K. S. Wan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Yat Tse
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Catherine Depew
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wan, J.K.S., Tse, M.Y. & Depew, M.C. CIDEP studies of the photolysis of the lignin model compound α-guaiacoxylacetoveratrone: the role of triplet reactions in aqueous and hydroxylic solvents. Res Chem Intermed 17, 59–75 (1992). https://doi.org/10.1163/156856792X00056

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1163/156856792X00056

Keywords

Search

Navigation