Advertisement

Route to the Siamese-Twin Porphyrin

  • Lina K. BluschEmail author
Chapter
  • 311 Downloads
Part of the Springer Theses book series (Springer Theses)

Abstract

I am not the first to conceive the structure of the Siamese-twin porphyrin. Already Lind and Katslaouni spent some effort to succeed in the synthesis of the described framework [1, 2]. Two main factors stymied progress in Lind’s 1987 dissertation: Firstly, the route to the key intermediate 1 was only feasible protecting the pyrazole-N1 with a benzylic protective group (Bn). However, its cleavage remained unsuccessful. The cyclization toward the Siamese-twin porphyrinogen 2 was still conducted, obtaining a mixture of regioisomers which could not be separated. Secondly, the following oxidation step of the left sp3 hybridized carbon atoms failed (Scheme 3.1). Katsiaouni also faced the latter problem and could not establish a reliable oxidation strategy.

Keywords

Nucleophilic Attack Cyclization Reaction Hybridize Carbon Atom Anhydrous CH2Cl2 Silica Column Chromatography 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    E. J. Lind, Ph.D.: Synthesis of the Tetrapyrrolic Macrocycle Octaazatetrahydro(1.5.1.5) Platyrin (Michigan State University, East Lansing, 1987)Google Scholar
  2. 2.
    S. Katsiaouni, Ph.D.: Neuartige Pyrrol/Pyrazol-Bausteine für die Synthese von Hybrid-Makrozyklen, azyklischen Ligandsystemen und bimetallischen Komplexen (Georg-August-Universität Göttingen, 2007)Google Scholar
  3. 3.
    P.D. Rao, S. Dhanalekshmi, B.J. Littler, J.S. Lindsey, J. Org. Chem. 65, 7323–7344 (2000)CrossRefGoogle Scholar
  4. 4.
    A. Sachse, L. Penkova, G. Noel, S. Dechert, O.A. Varzatskii, I.O. Fritsky, F. Meyer, Synthesis 5, 800–806 (2008)Google Scholar
  5. 5.
    L. K. Frensch, Diploma: Synthese von Pyrrol/Pyrazol-Hybrid-Bausteinen als Vorstufen zum Doppelporphyrin (Georg-August-Universität, Göttingen, 2008)Google Scholar
  6. 6.
    L.K. Frensch, K. Pröpper, M. John, S. Demeshko, C. Brückner, F. Meyer, Angew. Chem. Int. Ed. 50, 1420–1424 (2011)CrossRefGoogle Scholar
  7. 7.
    K. C. Majumdar, S. Mondal, Synlett 18, 2851–2855 (2008)Google Scholar
  8. 8.
    O. Meth-Cohn, E. Vuorinen, T.A. Modro, J. Org. Chem. 54, 4822–4827 (1989)CrossRefGoogle Scholar
  9. 9.
    H.G.O. Becker, R. Beckert, G. Domschke, E. Fanhänel, W.D. Habicher, P. Metz, D. Pavel, K. Schwetlick, Organikum, 21st edn. (Wiley-VCH, Weinheim, 2001)Google Scholar
  10. 10.
    G.D. Hartman, L.M. Weinstock, Org. Synth. 6, 620 (1988)Google Scholar
  11. 11.
    J.L. Sessler, A. Mazaffari, M.R. Johnson, Org. Synth. 9, 242 (1998)Google Scholar
  12. 12.
    H.-O. Kalinowski, S. Berger, S. Braun, Carbon 13 NMR Spectroscopy (Wiley, Weinheim, 1998)Google Scholar
  13. 13.
    E. Riedel, Moderne Anorganische Chemie, 3rd edn. (de Gruyter, Berlin, 2009)Google Scholar
  14. 14.
    K.M. Kadish, K.M. Smith, R. Guilard, The Porphyrin Handbook, vol. 1 (Academic Press, San Diego, 2000)Google Scholar
  15. 15.
    R.W. Boyle, C. Brückner, J. Posakony, B.R. James, D. Dolphin, Org. Synth. 76, 287–290 (1999)Google Scholar
  16. 16.
    L. Yu, K. Muthukumaran, I.V. Sazanovich, C. Kirmaier, E. Hindin, J.R. Diers, P.D. Boyle, D.F. Bocian, D. Holton, J.S. Lindsey, Inorg. Chem. 42, 6629–6647 (2003)CrossRefGoogle Scholar
  17. 17.
    G.R. Geier, J.S. Lindsey, J. Chem. Soc. Perkin Trans. 2, 677–686 (2001)Google Scholar
  18. 18.
    G.R. Geier, J.S. Lindsey, J. Chem. Soc. Perkin Trans. 2, 687–700 (2001)Google Scholar
  19. 19.
    G.R. Geier, B.J. Littler, J.S. Lindsey, J. Chem. Soc. Perkin Trans. 2, 701–711 (2001)Google Scholar
  20. 20.
    G.R. Geier, B.J. Littler, J.S. Lindsey, J. Chem. Soc. Perkin Trans. 2, 712–718 (2001)Google Scholar
  21. 21.
    G.R. Geier, J.A. Riggs, J.S. Lindsey, J. Porphyr. Phthalocyanines 5, 681–690 (2001)CrossRefGoogle Scholar
  22. 22.
    G.R. Geier, Y. Ciringh, F. Li, D.M. Haynes, J.S. Lindsey, Org. Lett. 2, 1745–1748 (2000)CrossRefGoogle Scholar
  23. 23.
    B.J. Littler, Y. Ciringh, J.S. Lindsey, J. Org. Chem. 64, 2864–2872 (1999)CrossRefGoogle Scholar
  24. 24.
    J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry (Oxford University Press, New York, 2001)Google Scholar

Copyright information

© Springer International Publishing Switzerland 2013

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of British ColumbiaVancouverCanada

Personalised recommendations