Skip to main content
SpringerLink
Log in

Electrophilic substitution in meso-phenylporphyrins

  • Selected articles originally published in Russian in Rossiiskii Khimicheskii Zhurnal (Russian Chemistry Journal)
  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Electrophilic substitution reactions in the meso-phenylporphyrins are described. The relative reactivity of the various positions of the porphyrin cycle to attack by electrophiles was discussed.

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. Kursunlu, A.N., RCS Adv. 2014. 4. p. 47690-47696.

    CAS  Google Scholar 

  2. Handbook of Porphyrin Science: With Application to Chemistry, Physics, Materials science, Engineering, Biology and Medicine, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., Hackensack, NJ: World Scientific, 2010, vol. 12.

  3. Fang, Y., Jiang, X., Ou, Z., Michelin, C., Desbois, N., Gros, C.P., and Kadish, K.M., J. Porphyrins Phthalocyanines, 2014, vol. 18, p. 832.

    Article  CAS  Google Scholar 

  4. Kralova, J., Kejik, Z., Briza, T., Pouckova, P., Kral, A., Martasek, P., and Kral, V., J. Med. Chem., 2010, vol. 53, p. 128.

    Article  CAS  Google Scholar 

  5. Horn, S., Dahms, K., and Senge, M.O., J. Porphyrins Phthalocyanines, 2008, vol. 12, p. 1053.

    Article  CAS  Google Scholar 

  6. Takanami, T., Hayashi, M., Chijimatsu, H., Inoue, W., and Suda, K., Org. Lett., 2005, vol. 7, p. 3937.

    Article  CAS  Google Scholar 

  7. Atefi, F., Locos, O.B., Senge, M.O. and Arnold, D.P., J. Porphyrins Phthalocyanines, 2006, vol. 10, p. 176.

    Article  CAS  Google Scholar 

  8. Van Belzen, R., Elsevier, C.J., Dedieu, A., Veldman, N., and Spek, A.L., Organometallics, 2003, vol. 22, p. 722.

    Article  Google Scholar 

  9. Hodgson, M.J., Borovkov, V.V., Inoue, Y., and Arnold, D.P., J. Organomet. Chem., 2006, vol. 691, p. 2162.

    Article  CAS  Google Scholar 

  10. Atefi, F., McMurtrie, J.C., Turner, P., Duriska, M., and Arnold, D.P., Inorg. Chem., 2006, vol. 45, p. 6479.

    Article  CAS  Google Scholar 

  11. Locos, O.B. and Arnold, D.P., Org. Biomol. Chem., 2006, vol. 4, p. 902.

    Article  CAS  Google Scholar 

  12. Takanami, T., Hayashi, M., Hino, F., and Suda, K., Tetrahedron Lett., 2003, vol. 44, p. 7353.

    Article  CAS  Google Scholar 

  13. Titov, D.V., Gening, M.L., Tsvetkov, Yu.E., and Nifantiev, N.E., Russ. Chem. Rev., 2014, vol. 83, no. 6, p. 523.

    Article  CAS  Google Scholar 

  14. Ethirajan, M., Chen, Y., Joshi, P., and Pandey, R., Chem. Soc. Rev., 2011, vol. 40, p. 340.

    Article  CAS  Google Scholar 

  15. Kralova, J., Kejik, Z., Briza, T., Pouckova, P., Kral, A., Martasek, P., and Kral, V., J. Med. Chem., 2010, vol. 53, p. 128.

    Article  CAS  Google Scholar 

  16. Silva, J.N., Silva, A.M.G., Tome, J.P., Ribeiro, A.O., Domingues, M.R.M., Cavaleiro, J.A.S., Silva, A.M.S., Neves, M.G., Tome, A.C., Serra, O.A., Bosca, F., Filipe, P., Santus, R., and Morliere, P., Photochem. Photobiol. Sci., 2008, vol. 7, p. 834.

    Article  CAS  Google Scholar 

  17. Kralova, J., Synytsya, A., Pouckova, P., Koc, M., Drovak, M., and Kral, V., Photochem. Photobiol., 2006, vol. 82, p. 432.

    Article  CAS  Google Scholar 

  18. Semeikin, A.S., Koifman, O.I., and Berezin, B.D., Khim. Geterotsikl. Soedin., 1986, no. 6, p. 798.

    Google Scholar 

  19. Crossley, M., Burn, P., Chew, S., Cuttance, F., and Newson, I., J. Chem. Soc. Chem. Commun., 1991, p. 1564.

    Google Scholar 

  20. Shen, D., Liu, C., and Chen, Q., Chem. Commun., 2005, p. 4982.

    Google Scholar 

  21. Kumar, D., Bhyrappa, P., and Varghese, B., Tetrahedron Lett., 2003, vol. 40, p. 4849.

    Article  Google Scholar 

  22. Balaji, T., Sasidharan, M., and Matsunaga, H., Analyst., 2005, vol. 130, p. 1162.

    Article  CAS  Google Scholar 

  23. Castriciano, M.A., Romeo, A., Villary, V., Angelini, N., Micali, N., and Monsu Scolaro, L., J. Phys. Chem. B, 2005, vol. 109, p. 12086.

    Article  CAS  Google Scholar 

  24. Czolk, R., Reichert, J., and Ache, H.J., Sens Actuators A Phys., 1991, 1A26, p. 439.

    Article  Google Scholar 

  25. Schwab, A.D., Smith, D.E., Rich, C.S., Young, E.R., Smith, W.F., and De Paula, J.C., J. Phys. Chem. B, 2003, vol. 107, p. 11339.

    Article  CAS  Google Scholar 

  26. Micali, N., Mallamace, F., Romeo, A., Purrello, R., and Monsu Scolaro, L., J. Phys. Chem. B, 2000, vol. 104, p. 5897.

    Article  CAS  Google Scholar 

  27. Chen, D.M., He, T., Cong, D.F., Zhang, Y.H., and Liu, F.C., J. Phys. Chem. A, 2001, vol. 105, p. 3981.

    Article  CAS  Google Scholar 

  28. Takahashi, A. and Mukamel, S., J. Chem. Phys., 1995, vol. 103, p. 7144.

    Article  CAS  Google Scholar 

  29. Jeukens, C., Lensen, M.C., Wijnen, F.J.P., Elemans, J., Christianen, P.C.M., Rowan, A.E., et al., Nano Lett., 2004, vol. 4, p. 1401.

    Article  CAS  Google Scholar 

  30. Schwab, A.D., Smith, D.E., Bond-Watts, B., Johnston, D.E., Hone, J., Johnson, A.T., et al., Nano Lett., 2004, vol. 4, p. 1261.

    Article  CAS  Google Scholar 

  31. Winkelman, J., Cancer Res., 1962, vol. 22, no. 5, p. 589.

    CAS  Google Scholar 

  32. Pasternak, R. F., Huber, P.R., Boyd, P., et. al., J. Am. Chem. Soc., 1972, vol. 94, no. 13, p. 4511.

    Article  Google Scholar 

  33. Radnyuk, V.S., Lyubimova, T.V., and Semeikin, A.S., Abstracts of Papers, 19 All-Russian Chugaev Meeting on Chemistry of Complex Compounds, Ivanovo, 1999, p. 171.

    Google Scholar 

  34. Bykova, V., Usoltseva, N., Ananjeva, G., Semeikin, A., and Karmanova, T., Mol. Cryst. Liq. Cryst., 1995, vol. 265, no. 1, p. 651.

    Article  Google Scholar 

  35. Rubires, R., Crusats, J., El-Hachemi, Z., Jaramillo, T., Lopez, M., Vails, E., Farrera, J.A., and Ribo, J.M., New J. Chem., 1999, vol. 23, no. 2, p. 189.

    Article  CAS  Google Scholar 

  36. Biffinger, J.C., Sun, H., Nelson, A.P., and DiMagno, S.G., Org. Biomol. Chem., 2003, vol. 1, no. 4, p. 733.

    Article  CAS  Google Scholar 

  37. Mandon, D., Ochsenbein, P., Fisher, J., Weiss, R., Jayaraj, K., Austin, R.N., Gold, A., White, P.S., Brigaud, O., Battioni, P., and Mansuy, D., Inorg. Chem., 1992, vol. 31, no. 11, p. 2044.

    Article  CAS  Google Scholar 

  38. Fernandes, A., A., Stinson, C.M., and Shamim, A., J. Sci. Ind. Res., 1987, vol. 30, no. 9, p. 643.

    CAS  Google Scholar 

  39. Chen, X., Tang, F., and Wang, C., Phys. Test. Chem. Anal., 1990, vol. 26, no. 2, p. 70.

    CAS  Google Scholar 

  40. Tang, F. Chen, X., and Wang, C., Huaxue Shiji (Chem. Reagents), 1987, vol. 9, no. 1, p. 7.

    Google Scholar 

  41. Zipplies, M.F., Lee, W.A., and Bruice, A.A., J. Am. Chem. Soc., 1986, vol. 108, no. 15, p. 4433.

    Article  CAS  Google Scholar 

  42. Lee, W.A., Gratzel, M., and Kalyanasundaram, K., Chem. Phys. Lett., 1984, vol. 107, no. 3, p. 308.

    Article  CAS  Google Scholar 

  43. Tang, F., Wang, L., and Chai, Z., Huaxue Shiji (Chem. Reagents), 1993, vol. 15, no. 6, p. 324.

    CAS  Google Scholar 

  44. Kruper, W.J., Chamberlin T.A., and Kochanny, M., J. Org. Chem., 1989, vol. 54, no. 11, p. 2753.

    Article  CAS  Google Scholar 

  45. Garcia-Ortega, H. and Ribo, J.M., J. Porphyrins Phthalocyanines, 2000, vol. 4, no. 5, p. 564.

    Article  CAS  Google Scholar 

  46. Ostrowski, S. and Lopuszynska, B., Synth. Commun., 2003, vol. 33, no. 23, p. 4101.

    Article  CAS  Google Scholar 

  47. Meng, G.G., James, B.R., and Skov, K.A.J., Can. J. Chem., 1994, vol. 72, p. 1894.

    Article  CAS  Google Scholar 

  48. Jaquinod, L., The Porphyrin Handbook, Kadish, K.M., Smith, K.M., and Guilard, R., Eds., New York: Academic, 2000, vol. 1, p. 201.

    CAS  Google Scholar 

  49. Luguya, R., Jaquinod, L., Fronczek, F.R., Vicente, M.G.H., and Smith, K.M., Tetrahedron, 2004, vol. 60, no. 12, p. 2757.

    Article  CAS  Google Scholar 

  50. Kolodina, E.A., Semeykin, A.S., and Syrbu, S.A., Abstracts of Papers, 5 Int. Conf. on Porphyrins and Phthalocyanines (ICPP-5), Moscow, 2008, p. 426.

    Google Scholar 

  51. Kolodina, E.A., Syrbu, S.A., Semeikin, A.S., and Koifman, O.I., Russ. J. Org. Chem., 2010, vol. 46, no. 1, p. 138.

    Article  CAS  Google Scholar 

  52. Lyubimtsev, A.V., Syrbu, S.A., Zheglova, N.V., Semeikin, A.S., and Koifman, O.I., Macroheterocycles, 2011, vol. 4, no. 4, p. 265.

    Article  CAS  Google Scholar 

  53. Syrbu, S., Lyubimtsev, A., Koifman, O., Ivanov, D., Noskov, S., Zheglova, N., Ugarov, V., and Smirnova, E., Abstracts of Papers, 7 Int. Conf. on Porphyrins and Phthalocyanines (ICPP-7), Jeju, Korea, 2012, p. 505.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ivanovo State University of Chemical Technology, Sheremetevskii pr. 7, Ivanovo, 153000, Russia

    S. A. Syrbu, A. V. Lyubimtsev, D. A. Ivanov, V. S. Ugarov & O. I. Koifman

Authors
  1. S. A. Syrbu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Lyubimtsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. A. Ivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. S. Ugarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. O. I. Koifman
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. A. Syrbu.

Additional information

Original Russian Text © S.А. Syrbu, А.V. Lyubimtsev, D.А. Ivanov, V.S. Ugarov, O.I. Koifman, 2014, published in Rossiiskii Khimicheskii Zhurnal, 2014, Vol. 58, Nos. 5–6, pp. 30–41.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Syrbu, S.A., Lyubimtsev, A.V., Ivanov, D.A. et al. Electrophilic substitution in meso-phenylporphyrins. Russ J Gen Chem 86, 2180–2192 (2016). https://doi.org/10.1134/S1070363216090334

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363216090334

Search

Navigation