A Tin-Complexation Strategy for Use with Diverse Acylation Methods in the Preparation of 1,9-Diacyldipyrromethanes

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 765-777

  Tamaru, Shun Ichi ^a   Yu, Lianhe ^a   Youngblood, W Justin ^a   Muthukumaran, Kannan ^a   Taniguchi, Masahiko ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; CATALYSIS; CHROMATOGRAPHIC ANALYSIS; COMPLEXATION; CONDENSATION; CRYSTALLIZATION; ORGANOMETALLICS; PURIFICATION; SYNTHESIS (CHEMICAL); TIN;

CRUDE REACTION MIXTURES;

PORPHYRINS;

1,9 DIACYLDIPYRROMETHANE DERIVATIVE; DIBUTYL (5,10 DIHYDRODIPYRRINATO)TIN COMPLEX; PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE; TIN; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTALLIZATION; FRIEDEL CRAFTS REACTION; GRIGNARD REACTION; MOLECULAR STABILITY; POLYMERIZATION; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS; TEMPERATURE DEPENDENCE; VILSMEIER HAACK REACTION;

ACYLATION; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; METHANE; METHANOL; MOLECULAR STRUCTURE; ORGANOTIN COMPOUNDS; PORPHYRINS; PYRROLES;

EID: 0842285782     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035622s     Document Type: Article

References (57)

1. Rao, P. D.; Dhanalekshmi, S.; Littler, B. J.; Lindsey, J. S. J. Org. Chem. 2000, 65, 7323-7344.
2. Rao, P. D.; Littler, B. J.; Geier, G. R., III; Lindsey, J. S. J. Org. Chem. 2000, 65, 1084-1092.
3. Anderson, H. J.; Loader, C. E. In Pyrroles. Part I; Jones, R. A.; Ed., John Wiley & Sons: New York, 1990; pp 397-497.
4. Cho, W.-S.; Lee, C.-H. Bull. Korean Chem. Soc. 1998, 19, 314-319.
5. Lee, C.-H.; Cho, W.-S. Tetrahedron Lett. 1999, 40, 8879-8882.
6. Cho, W.-S.; Kim, H.-J.; Littler, B. J.; Miller, M. A.; Lee, C.-H.; Lindsey, J. S. J. Org. Chem. 1999, 64, 7890-7901.
7. Maeda, H.; Osuka, A.; Ishikawa, Y.; Aritome, I.; Hisaeda, Y.; Furuta, H. Org. Lett. 2003. 5. 1293-1296.
8. Lee, C.-H.; Li, F.; Iwamoto, K.; Dadok, J.; Bothner-By, A. A.; Lindsey, J. S. Tetrahedron 1995, 51, 11645-11672.
9. (a) Cadamuro, S.; Degani, I.; Fochi, R.; Gatti, A.; Regondi, V. Synthesis 1987, 311-314.
10. (b) Barbero, M.; Cadamuro, S.; Degani, I.; Fochi, R.; Gatti, A.; Regondi, V. J. Org. Chem. 1988, 53, 2245-2250.
11. (a) Degani, I.; Fochi, R. J. Chem. Soc., Perkin Trans. 1 1976, 323-325.
12. (b) Barbero, M.; Cadamuro, S.; Degani, I.; Fochi, R.; Gatti, A.; Regondi, V. Synthesis 1986, 1074-1076.
13. Briñas, R. P.; Brückner, C. Tetrahedron 2002, 58, 4375-4381.
14. White, J.; McGillivray, G. J. Org. Chem. 1977, 42, 4248-4251.
15. Wallace, D. M.; Leung, S. H.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1993, 58, 7245-7257.
16. Gryko, D. T.; Tasior, M.; Koszarna, B. J. Porphyrins Phthalocyanines 2003, 7, 239-248.
17. Bröring, M. Synthesis 2000, 1291-1294.
18. Khoury, R. G.; Jaquinod, L.; Aoyagi, K.; Olmstead, M. M.; Fisher, A. J.; Smith, K. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2497-2500.
19. Brückner, C.; Posakony, J. J.; Johnson, C. K.; Boyle, R. W.; James, B. R.; Dolphin, D. J. Porphyrins Phthalocyanines 1998, 2, 455-465.
20. Boyle, R. W.; Karunaratne, V.; Jasat, A.; Mar, E. K.; Dolphin, D. Synlett 1994, 939-940.
21. Depraetere, S.; Dehaen, W. Tetrahedron Lett. 2003, 44, 345-347.
22. Kitamura, C.; Yamashita, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1443-1447.
23. Pommier, J. C.; Lucas, D. J. Organomet. Chem. 1973, 57, 139-153.
24. English, R. B.; McGillivray, G.; Smal, E. Acta Crystallogr. 1980, B36, 1136-1141.
25. Limage, M.-H.; Lautié, A.; Novak, A. C. R. Acad. Sci., Ser. B 1975, 280, 601-603.
26. Yagil, G. Tetrahedron 1967, 23, 2855-2861.
27. (a) Finkbeiner, H. J. Org. Chem. 1965, 30, 2861-2862.
28. (b) Chong, R.; Clezy, P. S.; Liepa, A. J.; Nichol, A. W. Aust. J. Chem. 1969, 22, 229-238.
29. Bennis, V.; Gallagher, J. F. Acta Crystallogr. 1998, C54, 130-132.
30. Lee, C.-H.; Lindsey, J. S. Tetrahedron 1994, 50, 11427-11440.
31. (a) Khoury, R. G.; Jaquinod, L.; Paolesse, R.; Smith, K. M. Tetrahedron 1999, 55, 6713-6732.
32. (b) Paolesse, R.; Pandey, R. K.; Forsyth, T. P.; Jaquinod, L.; Gerzevske, K. R.; Nurco, D. J.; Senge, M. O.; Licoccia, S.; Boschi, T.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 3869-3882.
33. (c) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227-6238.
34. (d) Sessler, J. L.; Johnson, M. R.; Creager, S. E.; Fettinger, J. C.; Ibers, J. A. J. Am. Chem. Soc. 1990, 112, 9310-9329.
35. (e) Sessler, J. L.; Johnson, M. R. Angew. Chem., Int. Ed. Engl. 1987, 26, 678-680.
36. Speckbacher, M.; Yu, L.; Lindsey, J. S. Inorg. Chem. 2003, 42, 4322-4337.
37. Geier, G. R., III; Callinan, J. B.; Rao, P. D.; Lindsey, J. S. J. Porphyrins Phthalocyanines 2001, 5, 810-823.
38. Davis, A. G. Organotin Chemistry; VCH: Weinheim, 1997; pp 18-24.
39. (a) Tin and Organotin Compounds, A Preliminary Review; World Health Organization: Geneva, 1980.
40. (b) Cooney, J. J. Helgol. Meeresunters. 1995, 49, 663-677.
41. Boyer, I. J. Toxicology 1989, 55, 253-298.
42. (a) Barnes, J. M.; Stoner, H. B. Br. J. Ind. Med. 1958, 15, 15-22.
43. (b) Klimmer, O. R. Arzneim.-Forsch. 1969, 19, 934-939.
44. U. S. National Cancer Institute TR-183; Bioassay of Dibutyltin Diacetate for Possible Carcinogenicity, DHEW Publication 79-1739; National Cancer Institute:Washington, DC, 1979.
45. Neumann, W. P. The Organic Chemistry of Tin; John Wiley & Sons: London, 1970; pp 230-237.
46. (a) Ingham, R. K.; Rosenberg, S. D.; Gilman, H. Chem. Rev. 1960, 60, 459-539.
47. (b) Finholt, A. E.; Bond, A. C., Jr.; Wilzback, K. E.; Schlesinger, H. I. J. Am. Chem. Soc. 1947, 69, 2692-2696.
48. (a) Weinshenker, N. M.; Crosby, G. A.; Wong, J. Y. J. Org. Chem. 1975, 40, 1966-1971.
49. (b) Mercier, F. A. G.; Biesemans, M.; Altmann, R.; Willem, R.; Pintelon, R.; Schoukens, J.; Delmond, B.; Dumartin, G. Organometallics 2001, 20, 958-962.
50. 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, 1391-1396.
51. Tomizaki, K.-y.; Yu, L.; Wei, L.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2003, 68, 8199-8207.
52. (a) Honeybourne, C. L.; Jackson, J. T.; Simmonds, D. J.; Jones, O. T. G. Tetrahedron 1980, 36, 1833-1838.
53. (b) Chang, C. K. J. Org. Chem. 1981, 46, 4610-4612.
54. (c) Wickramasinghe, A.; Jaquinod, L.; Nurco, D. J.; Smith, K. M. Tetrahedron 2001, 57, 4261-4269.
55. Buhleier, E.; Wehner, W.; Vögtle, F. Chem. Ber. 1979, 112, 559-566.
56. Korshunov, M. A.; Bodnaryuk, F. N.; Fershtut, E. V. Zh. Org. Khim. 1967, 3, 140-143.
57. Littler, B. J.; Ciringh, Y.; Lindsey, J. S. J. Org. Chem. 1999, 64, 2864-2872.