N-confused tetraphenylporphyrin and tetraphenylsapphyrin formation in one-flask syntheses of tetraphenylporphyrin

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1596-1603

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

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAPHENYLPORPHYRIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 0033525814     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982068r     Document Type: Article

References (20)

1. Chmielewski, P. J.; Latos-Grazynski, L.; Rachlewicz, K.; Glowiak, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 779-781.
2. Furuta. H.; Asano, T.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 767-768.
3. Chmielewski, P. J.; Latos-Grazynski, L.; Rachlewicz, K. Chem. Eur. J. 1995, 1, 68-73.
4. Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32, 476.
5. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827-836.
6. (a) Latos-Grazynski, L.; Chmielewski, P. J. New J. Chem. 1997, 27, 691-700.
7. (b) Chmielewski, P. J.; Latos-Grazynski, L. Inorg. Chem. 1997, 36, 840-845.
8. Chmielewski, P. J.; Latos-Grazynski, L.; Glowiak, T. J. Am. Chem. Soc. 1996, 118, 5690-5701.
9. Chmielewski, P. J.; Latos-Grazynski, L. J. Chem. Soc., Perkin Trans. 2 1995, 503-509.
10. (a) Ishikawa, Y.; Yoshida, I.; Akaiwa, K.; Koguchi, E.; Sasaki, T.; Furuta, H. Chem. Lett. 1997, 453-454.
11. (b) Ariga, K.; Kunitake, T.; Furuta, H. J. Chem. Soc., Perkin Trans. 2 1996, 667-672.
12. Ghosh, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1028-1030.
13. Snyder, L. R.; Kirkland, J. J.; Glajch, J. L. Practical HPLC Method Development, Second Edition; John Wiley and Sons: New York, 1997; pp 744-745.
14. Wagner, R. W.; Li, F.; Du, H.; Lindsey, J. S. Org. Proc. Res. Dev. 1993, 3, 28-37.
15. Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1989, 54, 828-836.
16. Lindsey, J. S.; MacCrum, K. A.; Tyhonas, J. S.; Chuang, Y. Y. J. Org. Chem. 1994, 59, 579-587.
17. Li, F.; Yang, K.; Tyhonas, J. S.; MacCrum, K. A.; Lindsey, J. S. Tetrahedron 1997, 53, 12339-12360.
18. A report has appeared concerning the formation of tris(2,6-dinitro-4-tert-butylphenyl)corrole, but yield and complete analytical data have not been published. See: Rose, E.; Kossanyi, A.; Quelquejeu, M.; Soleilhavoup, M.; Duwavarn, F.; Bernard, N.; Lecas, A. J. Am. Chem. Soc. 1996, 118, 1567-1568.
19. After elution of NC-TPP, additional dark material remained on the column (largely, but not entirely, quinone and hydroquinone materials). No attempt was made to further fractionate that material to look for additional polar macrocyclic pigments.
20. Lindsey, J. S. In Metalloporphyrin-Catalyzed Oxidations; Montanari, F., Casella, L., Eds.; Kluwer Academic Publishers: The Netherlands, 1994; pp 49-86.