Tetraaryldimethoxybenziporphyrins. At the edge of carbaporphyrinoid aromaticity

Journal of Organic Chemistry

Volumn 72, Issue 17, 2007, Pages 6481-6492

  Lash, Timothy D ^a   Szymanski, Joseph T ^a   Ferrence, Gregory M ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATICITY; DIMETHOXYBENZIPORPHYRINS; ORGANOMETALLIC DERIVATIVES;

ALDEHYDES; HALOGENATION; ORGANOMETALLICS; REACTION KINETICS; SYNTHESIS (CHEMICAL); TOLUENE;

PORPHYRINS;

1,3 DIMETHOXYBENZENE; 2 METHYLRESORCINOL DIMETHYL ETHER; ACETATE SILVER; ALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; CHLOROFORM; ESTER DERIVATIVE; HALOGEN; LITHIUM; MACROCYCLIC COMPOUND; NICKEL COMPLEX; ORGANOMETALLIC COMPOUND; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE; SILVER DERIVATIVE; SODIUM BOROHYDRIDE; TOLUENE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 34547948437     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070947k     Document Type: Article

References (53)

1. (a) Linstead, R. P. J. Chem. Soc. 1953, 2873-2884.
2. (b) Wu, R.; Cetin, A.; Durfee, W. S.; Ziegler, C. J. Angew. Chem., Int. Ed. 2006, 45, 5670-5673.
3. Berlin, K.; Breitmaier, E. Angew. Chem., Int. Ed. Engl. 1994, 33, 1246-1247.
4. Lash, T. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2533-2535.
5. Lash, T. D.; Chaney, S. T.; Richter, D. T. J. Org. Chem. 1998, 63, 9076-9088.
6. Lash, T. D. Synlett 2000, 279-295.
7. Richter, D. T.; Lash, T. D. Tetrahedron 2001, 57, 3659-3673.
8. See also: Miyake, K.; Lash, T. D. Chem. Commun. 2004, 178-179.
9. Liu, D.; Lash, T. D. J. Org. Chem. 2003, 68, 1755-1761.
10. (a) Lash, T. D.; Chaney, S. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 839-840.
11. (b) Graham, S. R.; Colby, D. A.; Lash, T. D. Angew. Chem., Int. Ed. 2002, 41, 1371-1374.
12. (c) Lash, T. D.; Colby, D. A.; Graham, S. R.; Chaney, S. T. J. Org. Chem. 2004, 69, 8851-8864.
13. Lash, T. D. Chem. Eur. J. 1996, 2, 1197-1200.
14. (a) Sessler, J. L.; Johnson, M. R.; Lynch, V. J. Org. Chem. 1987, 52, 4394-4397.
15. (b) Lash, T. D. J. Porphyrins Phthalocyanines 1997, 1, 29-44.
16. Colby, D. A.; Lash, T. D. Chem. Eur. J. 2002, 8, 5397-5402.
17. Lash, T. D.; Colby, D. A.; Ferrence, G. M. Eur. J. Org. Chem. 2003, 4533-4548.
18. Stepien, M.; Latos-Grazynski, L. Chem. Eur. J. 2001, 7, 5113-5117.
19. El-Beck, J. A.; Lash, T. D. Org. Lett. 2006, 8, 5263-5266.
20. Stepien, M.; Latos-Grazynski, L.; Szterenberg, L.; Panek, J.; Latajka, Z. J. Am. Chem. Soc. 2004, 126, 4566-4580.
21. Stepien, M.; Latos-Grazynski, L. Acc. Chem. Res. 2005, 38, 88-98.
22. (a) Graham, S. R.; Ferrence, G. M.; Lash, T. D. Chem. Commun. 2002, 894-895.
23. (b) Muckey, M. A.; Szczepura, L. F.; Ferrence, G. M.; Lash, T. D. Inorg. Chem. 2002, 41, 4840-4842.
24. Preliminary communication: Szymanski, J. T.; Lash, T. D. Tetrahedron Lett. 2003, 44, 8613-8616.
25. These results were presented, in part, at the following meetings: (a) Szymanski, J. T.; Lash, T. D. Program and Abstracts, 35th Great Lakes Regional American Chemical Society Meeting, Loyola University, Chicago, IL, June 2003; American Chemical Society: Washington, DC, 2003; Abstract No. 216.
26. (b) Szymanski, J. T.; Lash, T. D. Book of Abstracts, 227th National ACS Meeting, Anaheim, CA, March 28-April 1, 2004; American Chemical Society: Washington, DC, 2004; ORGN 147.
27. (c) Szymanski, J. T.; Lash, T. D. Program and Abstracts, 36th Great Lakes Regional American Chemical Society Meeting, Peoria, IL, October 2004; American Chemical Society: Washington, DC, 2004; Abstract No. 315.
28. Worden, L. R.; Kaufman, K. D.; Smith, P. J.; Widiger, G. N. J. Chem. Soc. (C) 1969, 227-230.
29. Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1989, 54, 828-836.
30. (a) Lash, T. D.; Novak, B. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 683-685.
31. (b) Lash, T. D.; Chandrasekar, P. J. Am. Chem. Soc. 1996, 118, 8767-8768.
32. (c) Spence, J. D.; Lash, T. D. J. Org. Chem. 2000, 65, 1530-1539.
33. Geier, G. R., III; Lindsey, J. S. J. Chem. Soc, Perkin Trans. 2 2001, 677-686.
34. Wannere, C. S.; Corminboeuf, C.; Allen, W. D.; Schaefer, H. F., III; Schleyer, P. v. R. Org. Lett. 2005, 7, 1457-1460.
35. Müllen, K.; Meul, T.; Schade, P.; Schmickler, H.; Vogel, E. J. Am. Chem. Soc. 1987, 109, 4992-5003.
36. Steiner, E.; Soncini, A.; Fowler, P. W. Org. Biomol. Chem. 2005, 3, 4053-4059.
37. Stepien, M.; Latos-Grazynski, L.; Lash, T. D.; Szterenberg, L. Inorg. Chem. 2001, 40, 6892-6900.
38. Dischendorfer, O.; Verdino, A. Monatsh. Chem. 1935, 66, 255-284.
39. Allen, F. H. Acta Crystallogr. 2002, B58, 380-388; Cambridge Structural Database, version 5.28 (Nov 2006).
40. Pawlicki, M.; Latos-Grazynski, L. Chem. Eur. J. 2003, 9, 4650-4660.
41. Xiao, Z.; Patrick, B. O.; Dolphin, D. Chem. Commun. 2002, 1816-1817.
42. Schmidt, I.; Chmielewski, P. J.; Ciunik, Z. J. Org. Chem. 2002, 67, 8917-8927.
43. As a counterpoint to our observations, it is worth noting that 22-hydroxytetraphenylbenziporphyrin tautomerizes to give an antiaromatic ketone that affords paratropic proton NMR chemical shifts: Stepien, M.; Latos-Grazynski, L.; Szterenberg, L. J. Org. Chem. 2007, 72, 2259-2270.
44. For a related azuliporphyrin derivative, see: Colby, D. A.; Ferrence, G. M.; Lash, T. D. Angew. Chem., Int. Ed. 2004, 43, 1346-1349.
45. (a) Bruker SMART 1000 CCD software package; Bruker Advanced X-ray Solutions: Madison, WI, 1999.
46. (b) Bruker SAINT Integration Software for Single Crystal Data frames - h,k,l, intensity; Bruker Advanced X-ray Solutions: Madison, WI, 1999.
47. (c) Bruker. SADABS-Empirical absorption correction produces; Bruker Advanced X-ray Solutions: Madison, WI, 1999.
48. McArdle, P. J. Appl. Crystallogr. 1996, 29, 306.
49. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
50. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Crystallog. 2005, 38, 381.
51. Sheldrick, G. M., SHELX-97, Programs for Crystal Structure Analysis (Release 97-2), Institüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1998.
52. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
53. Crystallographic data (excluding structure factors) for 16a has been deposited with the Cambridge Crystallographic Data Center as supplementary publication number CCDC 645634. Copies of this data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [fax: +44 (0)12233 336033 or e-mail: deposit@ccdc.cam.ac.uk].