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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.

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Reaction of pyrrole with aldehydes – a mysterious story

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  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.

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  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.

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  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.

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  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.

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  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.

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  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

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