Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Studies of Porphyrin Synthesis through 3+1 Condensation

  • Published : 20000100
Download PDF
⟨ Previous Next ⟩

Abstract

Acid-catalyzed porphyrin formation from meso-aryltripyrromethanes and $25-bis({\alpha}$, - hydroxyl - $\alpha$ -phenyl) methylfuran is studied. The condensation resulted in selective scrambling of tripyrromethanes when the condensation was carried out with catalytic amounts of $BF_3$ in methylene chloride. But the reaction carried out with p-TsOH or $BEt_3$ catalysts in the presence of $NH_4Cl$ in acetonitrile, single porphyrin product was isolated without scrambling of starting tripyrromethane. The yields of porphyrin in these studies were somewhat lower than those of 2+2 condensations or aldehyde-pyrrole condensations.

Keywords

References

  1. J. Am. Chem. Soc. v.63 Rothemund, P.; Menotti, A. R.
  2. J. Am. Chem. Soc. v.86 Adler, A. D.; Longo, F. R.; Shergalis, W.
  3. J. Org. Chem. v.32 Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.;Assour, J.; Korsakoff, L.
  4. J. Am. Chem. Soc. v.94 Kim, J. B.; Leonard, J. J.; Longo, J. D.
  5. J. Org. Chem. v.52 Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P.C.; Marguerettaz, A. M.
  6. J. Org. Chem. v.59 Lindsey, J. S.; MacCrum, K. A.; Tyhonas, J. S.; Chuang,Y. Y.
  7. J. Org. Chem. v.54 Lindsey, J. S.; Wagner, W. W.
  8. J. Org. Chem. v.64 Cho, W. S.; Kim, H. J.; Littler, B. J.; Miller, M. A.; Lee, C.H.; Lindsey, J. S.
  9. J. Org. Chem. v.64 Littler, B. J.; Cringh, Y.; Lindsey, J. S.
  10. J. Chem. Soc. Perkin Trans. I Ulman, A.; Manassen, J.
  11. J. Am. Chem. Soc. v.97 Ulman, A.; Manassen, J.
  12. Tetrahedron v.50 Lee, C. H.; Lindsey, J. S.

Cited by

  1. One-Flask Synthesis of Mono- and Trifunctionalized 21-Thia and 21-Oxaporphyrin Building Blocks and Their Application in the Synthesis of Covalent and Noncovalent Unsymmetrical Porphyrin Arrays vol.69, pp.20, 2004, https://doi.org/10.1021/jo040178u
  2. Synthesis, spectral data, and crystal structure of two novel substitution patterns in dithiaporphyrins vol.11, pp.1, 2007, https://doi.org/10.1142/s1088424607000023
  3. Mono-functionalized Heteroporphyrin Building Blocks and Unsymmetrical Covalent and Non-covalent Porphyrin Dyads vol.58, pp.1, 2011, https://doi.org/10.1002/jccs.201190067
  4. Thiaporphyrins: from building blocks to multiporphyrin arrays vol.4, pp.16, 2000, https://doi.org/10.1039/c3ra45444d
  5. Heteroatom-Containing Porphyrin Analogues vol.117, pp.4, 2000, https://doi.org/10.1021/acs.chemrev.6b00496
  6. K 2 S 2 O 8 mediated synthesis of 5-aryldipyrromethanes and meso -substituted A 4 -tetraarylporphyrins vol.25, pp.7, 2000, https://doi.org/10.1142/s1088424621500619