1 / 33

Reaction of pyrrole with aldehydes – a mysterious story

Reaction of pyrrole with aldehydes – a mysterious story . Daniel T. Gryko Institute of Organic Chemistry of the Polish Academy of Sciences Warsaw, Poland. Ehrlich reagent. Variety of products.

garnet
Download Presentation

Reaction of pyrrole with aldehydes – a mysterious story

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Reaction of pyrrole with aldehydes – a mysterious story Daniel T. Gryko Institute of Organic Chemistry of the Polish Academy of Sciences Warsaw, Poland

  2. Ehrlich reagent

  3. Variety of products

  4. Fig. 1 A representative LD-MS spectrum from a crude oxidized reaction mixture of pyrrole + benzaldehyde (100 mM pyrrole + benzaldehyde, 10 mM BF3–Et2O, CH2Cl2, room temperature, 2 min). The oligomer length (n) is given by the number above the symbol. The yield of TPP (UV–Vis) is noted. Complexity

  5. Rothemund P. Rothemund J. Am. Chem. Soc.1935, 57, 2010. P. Rothemund J. Am. Chem. Soc.1936, 58, 625. P. Rothemund J. Am. Chem. Soc.1939, 61, 2912. P. Rothemund, A. R. Menotti J. Am. Chem. Soc.1941, 63, 267.

  6. Adler A. D. Adler, F. R. Longo, W. Shergalis J. Am. Chem. Soc.1964, 86, 3145. A. D. Adler, F. R. Longo and co-workers J. Org. Chem. 1967, 32, 476.

  7. Lindsey J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney et al J. Org. Chem. 1987, 52, 827. G. R. Geier III, J. A. Riggs, J. S. Lindsey JPP2001, 5,681.

  8. Lindsey J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney et al J. Org. Chem. 1987, 52, 827.

  9. Lindsey-salts • No correlation with cations. • No correlation with desiccative power. • Reversible or not??? F. Li, K. Yang, J. S. Tyhonas, K. A. MacCrum, J. S. Lindsey Tetrahedron1997, 53, 12339.

  10. Lindsey-salts F. Li, K. Yang, J. S. Tyhonas, K. A. MacCrum, J. S. Lindsey Tetrahedron1997, 53, 12339.

  11. Lindsey-deep G. R. Geier III, J. S. Lindsey Org. Lett. 2000, 2, 1745.

  12. Lindsey-st. hind. J. S. Lindsey, R. W. Wagner J. Org. Chem. 1989, 54, 828.

  13. Trans-A2B2-porphyrins J. S. Lindsey, R. W. Wagner J. Org. Chem. 1999, 64, 2864. D. T. Gryko, M. Tasior, TetrahedronLett. 2003, 44, 3317.

  14. Gas phase C. M. Drain, X. Gong Chem. Commun. 1997, 2117.

  15. Gas phase-2 C. M. Drain, et al. J. Porphyrins Phthalocyanines. 2010, 14, 621.

  16. Oxidative Lewis Acids E. F. LLama and co-workers J. Chem. Soc. Perkin 1 1995, 2611.

  17. In phenols G. A. Mirafzal, H. M. Bosse, J. M. Summer Tetrahedron Lett. 1999, 40, 623.

  18. In micelles R. P. Bonar-Law J. Org. Chem 1996, 61, 3623.

  19. Rocha-Gonzalves M. d’A. Rocha Gonzalves and co-workers J. Het. Chem. 1985, 22, 931.

  20. Rocha-Gonzalves M. d’A. Rocha Gonzalves and co-workers Heterocycles1996, 43, 1423. M. d’A. Rocha Gonzalves and co-workersJPP,2007, 11, 77-84.

  21. Sharghi H. Sharghi, A. H. Nejad Helv. Chim. Acta2003, 86, 408. H. Sharghi, A. H. Nejad Tetrahedron2004, 60, 1863.

  22. Krausz P. Krausz et al. J. PorphyrinsPkthalocyanines2006, 10, 937. P. Krausz et al. TetrahedronLett. 2008, 49, 5537.

  23. Furuta/Lotos L. Latos-Grażyński and co-workers Angew. Chem. Int. Ed.. 1994, 33, 779. H. Furuta, H. Osano, T. Ogawa J. Am. Chem. Soc. 1994, 116, 767.

  24. Lindsey N-confused G. R. Geier III, J. S. Lindsey J. Org. Chem. 1999, 64, 1596. J. S. Lindsey, K. A. MacCrum, J. S. Tyhonas, Y.-Y. Chuang J. Org. Chem. 1994, 59,579. G. R. Geier III, D. M. Haynes, J. S. Lindsey Org. Lett. 1999, 1, 1455.

  25. Lindsey N-confused G. R. Geier III, D. M. Haynes, J. S. Lindsey Org. Lett. 1999, 1, 1455.

  26. Cavaleiro J. A. S. Cavaleiro and coworkers Chem. Commun. 1999, 385.

  27. Cavaleiro J. A. S. Cavaleiro and coworkers Chem. Commun. 1999, 385.

  28. Osuka-1 J.-Y. Shin, H. Furuta, K. Yoza, S. Igarashi, A. Osuka J. Am. Chem. Soc. 2001, 123, 7190.

  29. Osuka-2 J.-Y. Shin, H. Furuta, K. Yoza, S. Igarashi, A. Osuka J. Am. Chem. Soc. 2001, 123, 7190. S. Shimizu, J.-H. Shin, H. Furuta, R. Ismael, A. Osuka Angew. Chem. Int. Ed.. 2003, 42, 78.

  30. Who was first? N. M. Loim and co-workers Izv. Akad. Nauk. Ser. Khim. 1994, 5, 925. E. Rose and co-workers J. Am. Chem. Soc. 1996, 118, 1567. L. Latos-Grażyński and co-workers New J. Chem. 1997, 21, 691.

  31. No catalyst… G. I. Zhungietu, F. N. Chukhrii Zh. Vses. Khim. Obshchest. 1970, 15, 586. T. Severin, I. Ipach Chem. Ber. 1975, 108, 1768. S. P. Ivonin, A. V. Lapandin, A. A. Anishchenko Synth. Comm. 2004, 34, 451.

  32. With base… S. Taniguchi and co-workers Synlett1999, 73.

  33. Summary • We utilize the reaction which we do not understand • More accidental than rational development • Probably still at the early stage

More Related