Solvent-free condensation of pyrrole and pentafluorobenzaldehyde: A novel synthetic pathway to corroie and oligopyrromethenes

Organic Letters

Volumn 1, Issue 4, 1999, Pages 599-602

  Gross, Zeev ^a   Galili, Nitsa ^a   Simkhovich, Liliya ^a   Saltsman, Irena ^a   Botoshansky, Mark ^a   Blǎser, Dieter ^b   Boese, Roland ^b   Goldberg, Israel ^c  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b UNIVERSITY OF DUISBURG ESSEN   (Germany)

^c TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000534548     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990739h     Document Type: Article

References (23)

1. Lindsey, J. S. Metalloporphyrins Catalyzed Oxidations; Montanari, F., Casella, L., Eds.; Kluwer: Dordrecht, 1994; pp 49-86 and references therein.
2. Li, F. R.; Yang, K. X.; Tyhonas, J. S.; MacCrum, K. A.; Lindsey, J. S. Tetrahedron 1997, 53, 12339. Wagner, R. W.; Johnson, T. E.; Lindsey, J. S. Tetrahedron 1997, 53, 6755.
3. Li, F. R.; Yang, K. X.; Tyhonas, J. S.; MacCrum, K. A.; Lindsey, J. S. Tetrahedron 1997, 53, 12339. Wagner, R. W.; Johnson, T. E.; Lindsey, J. S. Tetrahedron 1997, 53, 6755.
4. (a) Sessler, J. L.; Weghom, S. J. In Expanded, Contracted, & Isomeric Porphyrins; Pergamon: Oxford, 1997; pp 1-505.
5. (b) Reference 3a, pp 11-55.
6. Licoccia, S.; Paolesse, R. Struct. Bond. 1995, 84, 71-133.
7. Paolesse, R.; Licoccia, S.; Fanciullo, M.; Morgante, E.; Boschi, T. Inorg. Chim. Acta 1993, 203, 107.
8. Rothmund, P.; Menotti, A. R. J. Am. Chem. Soc. 1941, 63, 267.
9. (a) For a recent review on solvent-free reactions, see: Toda, F. Acc. Chem. Res. 1995, 28, 480.
10. (b) For trace amounts of corroies in the Rothmund and Lindsey procedures, see: Rose, E.; Kossanyi, A.; Quelquejeu, M.; Soleilhavoup, M.; Duwavran, F.; Bernard, N.; Lecas, A. J. Am. Chem. Soc. 1996, 118, 1567. Latos-Grazynsky, L.; Chmielewski, P. J. New J. Chem. 1997, 21, 691.
11. (b) For trace amounts of corroies in the Rothmund and Lindsey procedures, see: Rose, E.; Kossanyi, A.; Quelquejeu, M.; Soleilhavoup, M.; Duwavran, F.; Bernard, N.; Lecas, A. J. Am. Chem. Soc. 1996, 118, 1567. Latos-Grazynsky, L.; Chmielewski, P. J. New J. Chem. 1997, 21, 691.
12. Gross, Z.; Galili, N.; Saltsman, I. Angew. Chem. 1999, 38, 1427.
13. (a) For isolation of the zinc(II) complex of 1b in a modified Rothmund procedure, see: Hill, C. L.; Williamson, M. M. J. Chem. Soc., Chem. Commun. 1985, 1228.
14. (b) For synthesis of the somewhat related dipyrromethanes (the bridging carbon is saturated and there is only one aryl) under a modified Lindsey procedure, see: Littler, B. J.: Miller, M. A.; Hung, C. H.; Wagner, R. W.; O'Shea, D. F.; Boyle, P. D.; Lindsey, J. S. J. Org. Chem. 1999, 64, 1391.
15. Kim, J. B.; Adler, A. D.; Longo, F. R. In The Porphyrins, Vol. I.; Dolphin, D., Ed.; Academic Press: New York, 1979; pp 90-96.
16. (a) For the structural characterization of larger oligomers with direct pyrrole-pyrrole linkages (up to nine pyrroles), see: Morisini, P.; Schere, M.; Meyer, S.; Lynch, V.; Sessler, J. L. J. Org. Chem. 1997, 62, 8848.
17. (b) For a not well resolved structure of a methene-only bridged pentamer with three pyrroles and two pyrrolidones, see: Wagner, U. G.; Kratsky, C.; Falk, H.; Flodl, H. Monatsh. Chem. 1987, 118, 1185.
18. Nogales, D. F.; Anstine, D. T.; Lightner, D. A. Tetrahedron 1994, 50, 8579 and references therein.
19. Reference 3a, Chapter 8.
20. Harrison, H. R.; Hodder, O. J. R.; Hodgkin, D. C. J. Chem. Soc. B 1971, 640.
21. Gross, Z.; Simkhovich, L.; Galili N. J. Chem. Soc., Chem. Commun. 1999, 599.
22. 3 has recently become commercially available, by Strem Chemicals.
23. (b) Gross, Z. (Technion) IL-A 126426.