Effects of diverse acid catalysts on the reaction course in the two-step one-flask synthesis of meso-tetraphenylporphyrin

Journal of Porphyrins and Phthalocyanines

Volumn 6, Issue 3, 2002, Pages 159-185

  Geier III, G Richard ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

Acid catalysis; Br nsted acid; Lewis acid; Mass spectrometry; N confused tetraphenylporphyrin; Porphyrin; Pyrromethane; Tetraphenylporphyrin; Tetraphenylsapphyrin

Indexed keywords

ACID; COPPER DERIVATIVE; ETHER DERIVATIVE; LEWIS ACID; PHENYL GROUP; TETRAPHENYLPORPHYRIN DERIVATIVE; TETRAPHENYLSAPPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 0036386406     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424602000208     Document Type: Article

References (50)

1. Lindsey JS. In The Porphyrin Handbook, Vol. 1, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: New York, 2000; pp 45-118.
2. Lindsey JS. In Metalloporphyrins catalysed Oxidations, Montanari F, Casella L. (Eds.) Kluwer Academic: Dordrecht, the Netherlands, 1994; p 49.
3. Lindsey JS, Schreiman IC, Hsu HC, Kearney PC and Marguerettaz AM. J. Org. Chem. 1987; 52: 827-836.
4. Lindsey JS and Wagner RW. J. Org. Chem. 1989; 54: 828-836.
5. Wagner RW, Li F, Du H and Lindsey JS. Org. Process Res. & Dev. 1999; 3: 28-37.
6. Li F, Yang K, Tyhonas JS, MacCrum KA and Lindsey JS. Tetrahedron 1997; 53: 12339-12360.
7. Geier GR, III and Lindsey JS. J. Org. Chem. 1999; 64: 1596-1603.
8. Lindsey JS, MacCrum KA, Tyhonas JS and Chuang YY. J. Org. Chem. 1994; 59: 579-587.
9. Onaka M, Shinoda T, Izumi Y and Nolen E. Chem. Lett. 1993: 117-120.
10. Onaka M, Shinoda T, Izumi Y and Nolen E. Tetrahedron Lett. 1993; 34: 2625-2628.
11. Laszlo P and Luchetti J. Chem. Lett. 1993: 449-452.
12. Shinoda T, Izumi Y and Onaka M. J. Chem. Soc., Chem. Commun. 1995: 1801-1802.
13. Shinoda T, Onaka M and Izumi Y. Chem. Lett. 1995: 493-494.
14. Wijesekera TP. Can. J. Chem. 1996; 74: 1868-1871.
15. Freeman BA and Smith KM. Synth. Commun. 1999; 29: 1843-1855.
16. Littler BJ, Ciringh Y and Lindsey JS. J. Org. Chem. 1999; 64: 2864-2872.
17. Rao PD, Littler BJ, Geier GR, III and Lindsey JS. J. Org. Chem. 2000; 65: 1084-1092.
18. Rao PD, Dhanalekshmi S, Littler BJ and Lindsey JS. J. Org. Chem. 2000; 65: 7323-7344.
19. Gunter MJ and Mander LN. J. Org. Chem. 1981; 46: 4792-4795.
20. Baldwin JE, Crossley MJ, Klose T, O'Rear EA, III and Peters MK. Tetrahedron 1982; 38: 27-39.
21. Osuka A, Nagata T, Kobayashi F and Maruyama K. J. Heterocycl. Chem. 1990; 27: 1657-1659.
22. Jackson AH, Pandey RK, Rao KRN and Roberts E. Tetrahedron Lett. 1985; 26: 793-796.
23. Pichon C and Scott AI. Tetrahedron Lett. 1994; 35: 4497-4500.
24. Srinivasan A, Mahajan S, Pushpan SK, Ravikumar M and Chandrashekar TK. Tetrahedron Lett. 1998; 39: 1961-1964.
25. Geier GR, III and Lindsey JS. J. Chem. Soc., Perkin Trans. 2 2001: 677-686.
26. Geier GR, III and Lindsey JS. J. Chem. Soc., Perkin Trans. 2 2001: 687-700.
27. Geier GR, III, Littler BJ and Lindsey JS. J. Chem. Soc., Perkin Trans. 2 2001: 701-711.
28. Geier GR, III, Littler BJ and Lindsey JS. J. Chem. Soc., Perkin Trans. 2 2001: 712-718.
29. Cook D. Can. J. Chem. 1963; 41: 522-526.
30. Childs RF, Mulholland DL and Nixon A. Can. J. Chem. 1982, 60: 801-808.
31. Carlson R, Lundstedt T, Nordahl A and Prochazka M. Acta Chem. Scand. Ser. B 1986; B40: 522-533.
32. Aldrichimica Acta 1986; 19: 76.
33. Kobayashi S. Eur. J. Org. Chem. 1999: 15-27.
34. Kobayashi S. Chem. Lett. 1991: 2187-2190.
35. Kobayashi S. Synlett 1994: 689-701.
36. Marshman RW. Aldrichimica Acta 1995; 28: 77-84.
37. Okuhara T, Hu C, Hashimoto M and Misono M. Bull. Chem. Soc. Jpn. 1994; 67: 1186-1188.
38. Geier GR, III, Ciringh Y, Li F, Haynes DM and Lindsey JS. Org. Lett. 2000; 2: 1745-1748.
39. Geier GR, III, Haynes DM and Lindsey JS. Org. Lett. 1999; 1: 1455-1458.
40. Geier GR, III, Callinan JB, Rao PD and Lindsey JS. J. Porphyrins Phthalocyanines 2001; 5: 810-823.
41. Geier GR, III, Riggs JA and Lindsey JS. J. Porphyrins Phthalocyanines 2001; 5: 681-690.
42. Rothemund P and Menotti AR. J. Am. Chem. Soc. 1941; 63: 267-270.
43. Adler AD, Longo FR and Shergalis W. J. Am. Chem. Soc. 1964; 86: 3145-3149.
44. Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J and Korsakoff L. J. Org. Chem. 1967; 32: 476.
45. Babu G and Perumal PT. Aldrichimica Acta 2000; 33: 16-22.
46. The yield of TPP is determined by removal of aliquots from the condensation mixture, treatment with DDQ, and quantitation by absorption spectroscopy. The "turnover in yield of TPP" reflects the decline in concentration of tetraphenylporphyrinogen, which is the precursor to TPP.
47. Both deviations may have been due to coincidental co-elution of the benzaldehyde and an intermediate or byproduct during TLC analysis. Additional developing solvents were examined, but the definitive identification of multiple species could not be made.
48. Sanders JKM, Bampos N, Clyde-Watson Z, Darling SL, Hawley JC, Kim H-J, Mak CC and Webb SJ. In The Porphyrin Handbook, Vol. 3, Kadish KM, Smith KM, Guilard R. (Eds.) Academic Press: New York, 2000; pp 1-48.
49. Rothemund P and Menotti AR. J. Am. Chem. Soc. 1948; 70: 1808-1812.
50. Lindsey JS and Woodford JN. Inorg. Chem. 1995; 34: 1063-1069.