Corrole synthesis by dipyrromethane-dicarbinol and 2,2′-bipyrrole condensation

Tetrahedron Letters

Volumn 44, Issue 16, 2003, Pages 3323-3327

  Decréau, Richard A ^a   Collman, James P ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

2,2 bipyrrole; Corrole synthesis; Dipyrromethane dicarbinol

Indexed keywords

2,2' BIPYRIDINE; 5,10,15 TRIS(4 METHYLPHENYL)CORROLE; 5,15 BIS(PHENYL) 10 (4 METHYLPHENYL)CORROLE; ACETONITRILE; ALCOHOL DERIVATIVE; METHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; MASS SPECTROMETRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0037436899     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00617-8     Document Type: Article

References (50)

1. Gross Z., Golubkov G., Simkhovich L. Angew. Chem., Int. Ed. 39:2000;4045-4047.
2. Gross Z., Simkhovich L., Galili N. Chem. Commun. 39:1999;599-600.
3. Simkhovich L., Gross Z. Tetrahedron Lett. 42:2001;8089-8092.
4. Simkhovich L., Mahammed A., Goldberg I., Gross Z. Chem. Eur. J. 7:2001;1041-1055.
5. Aviezer D., Cotton S., David M., Segev A., Khaselev N., Galili N., Gross Z., Yayon A. Cancer Res. 60:2000;2973-2980.
6. Kadish K.M., Ou Z., Shao J., Gros C.P., Barbe J.-M., Jerome F., Bolze F., Burdet F., Guilard F. Inorg. Chem. 41:2002;3990-4005.
7. Jerome F., Gros C.P., Tardieux C., Barbe J.-M., Guilard R. New J. Chem. 1998;1327-1329.
8. Johnson A.W., Kay I.T. J. Chem. Soc. 1965;1620-1629.
9. Gryko D.T. Eur. J. Org. Chem. 11:2002;1735-1743.
10. Paolesse R., Jaquinod L., Nurco D.J., Mini S., Sagone F., Boschi T., Smith K.M. Chem. Commun. 14:1999;1307-1308.
11. Paolesse R., Nardis S., Sagone F., Khoury R.G. J. Org. Chem. 66:2001;550-556.
12. Gross Z., Galili N., Saltsman I. Angew. Chem., Int. Ed. 38:1999;1427-1429.
13. Gross Z., Galili N., Saltsman I., Simkhovich L., Saltsman I., Botoshansky M., Blaser D., Boese R., Goldberg I. Org. Lett. 1:1999;599-602.
14. Collman J.P., Decreau R.A. Tetrahedron Lett. 44:2002;1207-1210.
15. Gryko D.T. Chem. Commun. 22:2000;2243-2244.
16. Gryko D.T., Jadach K. J. Org. Chem. 66:2001;4267-4275.
17. Gryko D.T., Piechota K.E. J. Porphyrins Phthalocyanines. 6:2002;81-97.
18. Cho W.S., Lee C.H. Tetrahedron Lett. 41:2000;697-701.
19. Sankar J., Anand V.G., Venkatraman S., Rath H., Chandrashekar T.K. Org. Lett. 4:2002;4233-4235.
20. Ka J.-W., Cho W.-S., Lee C.-H. Tetrahedron Lett. 41:2000;8121-8125.
21. Asokan C.V., Smeets S., Dehaen W. Tetrahedron Lett. 42:2001;4483-4485.
22. Brinas R.P., Bruckner C. Synlett. 3:2001;442-444.
23. Broring M., Hell C. Chem. Commun. 2001;2336-2337.
24. Tse M.K., Zhang Z., Mak T.C.W., Chan K.S. Chem. Commun. 1998;1199-2000.
25. (a) Broadhust, M. J.; Grigg, R.; Johnson, A. W. J. Chem. Soc., Perkin Trans. 1 1974, 1124-1135;
26. (b) Conlon, M.; Johnson, A. W.; Overend, W. R.; Rajapaksa, D.; Elson, C. M. J. Chem. Soc. Perkin Trans. 1 1973, 2281-2288;
27. (c) Vogel, E.; Broring, M.; Fink, J.; Rosen, D.; Schmiekler, H.; Lex, J.; Chan, K. W. K.; Wu, Y.-D.; Plattner, D. A.; Nendel, M.; Houk, K. N. Angew. Chem., Int. Ed. 1995, 34, 2514;
28. 3 and Geier's reports at ACS meeting: Geier, G. R., III; Grindrod, S. S.; Callinan, J. B.; Reid, C. G. Abstr. Papers Am. Chem. Soc. 2002, 224, 750;
29. (e) oxacorrole formation was reported as a side product from the condensation reaction of oxa-dipyrromethane dicarbinol with dipyrromethane: Lee, C.-H.; Cho, W.-S.; Ka, H.-J.; Lee, P. H. Bull. Korean Chem. Soc. 2000, 21, 429-433.
30. Cho W.-S., Kim H.-J., Littler B.J., Miller M.A., Lee C.-H., Lindsey J.S. J. Org. Chem. 64:1999;7890-7901.
31. Rao P.D., Dhanalekshmi S., Littler B.J., Lindsey J.S. J. Org. Chem. 65:2000;7323-7344.
32. Geier G.R., Littler B.J., Lindsey J.S. J. Chem. Soc., Perkin Trans. 2. 2001;712-718.
33. Geier G.R., Lindsey J.S. J. Chem. Soc., Perkin Trans. 2. 2001;687-700.
34. Gryco D., Lindsey J.S. J. Org. Chem. 65:2000;2249-2252.
35. Geier G.R., Callinan J.B., Rao P.D., Lindsey J.S. J. Porphyrins Phthalocyanines. 5:2001;810-823.
36. Wallace D.M., Leung S.H., Senge M.O., Smith K.M. J. Org. Chem. 58:1993;7245-7257.
37. Pawlicki M., Latos-Grazynski L., Szterenberg L. J. Org. Chem. 67:2002;5644-5653.
38. Latos-Grazynski L., Chmielewski P.-J. New J. Chem. 21:1997;691-700.
39. 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. 64:1999;1391-1396;
40. 3 through for 2 min or by extraction of ammonium hydroxide solution)) followed by recrystallization in hexane/dichloromethane 2/1 vol.
41. 12e mp 93-95°C.
42. f 0.40.
43. Itahara T. J. Chem. Soc., Chem. Commun. 1980;49-50.
44. Itahara T. J. Chem. Soc., Chem. Commun. 1981;254-255.
45. Itahara T. J. Org. Chem. 50:1985;5272-5275.
46. Itahara T. Heterocycles. 24:1986;2557-2562.
47. 17a mp 189-190°C).
48. f 0.51.
49. Lee C.-H., Li F., Iwamoto K., Dadok J., Bothner-By A.A., Lindsey J.S. Tetrahedron. 51:1995;11645-11672.
50. 4b,8c.