15N NMR chemical shifts for the identification of dipyrrolic structures

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 2964-2971

  Wood, Tabitha E ^a   Berno, Bob ^b   Beshara, Cory S ^a   Thompson, Alison ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; ZINC COMPOUNDS;

DIPYRROLIC STRUCTURES; ELECTRON-WITHDRAWING GROUPS; NMR CHEMICAL SHIFTS;

ORGANIC COMPOUNDS;

ALKENE DERIVATIVE; BORON DERIVATIVE; BROMIDE; METHANE; NITROMETHANE; PYRROLE DERIVATIVE; ZINC COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONJUGATION; ISOMERIZATION; NITROGEN NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 33645791590     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0524932     Document Type: Article

References (43)

1. Berger, S.; Braun, S.; Kalinowski, H.-O. NMR Spectroscopy of the Non-Metallic Elements; Wiley & Sons: Toronto, 1997.
2. Mason, J. Chem. Rev. 1981, 81, 205-227.
3. Hansen, P. E.; Jakobsen, H. J. Org. Magn. Reson. 1984, 22, 668-670.
4. Zhu, X. X.; Sauriol, F.; Brown, G. R. Can. J. Spectrosc. 1988, 33, 63-71.
5. Falk, H.; Mueller, N. Magn. Reson. Chem. 1985, 23, 353-357.
6. Laha, J. K.; Dhanalekshmi, S.; Taniguchi, M.; Ambroise, A.; Lindsey, J. S. Org. Process Res. Dev. 2003, 7, 799-812.
7. Halper, S. R.; Cohen, S. M. Inorg. Chem. 2005, 44, 486-488.
8. Sazanovich, I. V.; Kirmaier, C.; Hindin, E.; Yu, L.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Am. Chem. Soc. 2004, 126, 2664-2665.
9. Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 9th ed.; Molecular Probes Inc.: Eugene, OR, 2002.
10. Gabe, Y.; Urano, Y.; Kikuchi, K.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 3357-3367.
11. Kay, L. E.; Keifer, P.; Saarinen, T. J. Am. Chem. Soc. 1992, 114, 10663-10665.
12. Kontaxis, G.; Stonehouse, J.; Laue, E. D.; Keeler, J. J. Magn. Reson. A 1994, 111, 70-76.
13. Tamaru, S.-i.; Yu, L.; Youngblood, W. J.; Muthukumaran, K.; Taniguchi, M.; Lindsey, J. S. J. Org. Chem. 2004, 69, 765-777.
14. Wrackmeyer, B. J. Organomet. Chem. 1985, 297, 265-272.
15. Kitamura, C.; Yamashita, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1443-1447.
16. Li, Y.; Turnas, A.; Ciszewski, J. T.; Odom, A. L. Inorg. Chem. 2002, 41, 6298-6306.
17. Jones, R. A.; Bean, G. P. The Chemistry of Pyrroles; Organic Chemistry, Vol. 34; Academic Press: London, 1977.
18. Falk, H. The Chemistry of Linear Oligopyrroles and Bile Pigments; Springer-Verlag: New York, 1989.
19. Gust, D.; Roberts, J. D. J. Am. Chem. Soc. 1977, 99, 3637-3640.
20. Halper, S. R.; Cohen, S. M. Angew. Chem., Int. Ed. 2004, 43, 2385-2388.
21. Sutton, J. M.; Rogerson, E.; Wilson, C. J.; Sparke, A. E.; Archibald, S. J.; Boyle, R. W. Chem. Commun. 2004, 1328-1329.
22. Mothana, B.; Ban, F.; Boyd, R. J.; Thompson, A.; Hadden, C. E. Mol. Phys. 2005, 103, 1113-1129.
23. Harris, R. K.; Becker, E. D.; Cabral De Menezes, S. M.; Goodfellow, R.; Granger, P. Pure Appl. Chem. 2001, 73, 1795-1818.
24. Huggins, M. T.; Tipton, A. K.; Chen, Q.; Lightner, D. A. Monatsh. Chem. 2000, 131, 825-838.
25. Zhang, Y.; Ma, J. S. Org. Prep. Proced. Int. 2001, 33, 81-86.
26. Gryko, D.; Lindsey, J. S. J. Org. Chem. 2000, 65, 2249-2252.
27. Wood, T. E.; Ross, A. C.; Dalgleish, N. D.; Power, E. D.; Thompson, A.; Chen, X.; Okamoto, Y. J. Org. Chem. 2005, 70, 9967-9974.
28. Bruckner, C.; Karunaratne, V.; Rettig, S. J.; Dolphin, D. Can. J. Chem. 1996, 74, 2182-2193.
29. Al-Sheikh-Ali, A.; Cameron, K. S.; Cameron, T. S.; Robertson, K. N.; Thompson, A. Org. Lett. 2005, 7, 4773-4775.
30. Yu, L.; Muthukumaran, K.; Sazanovich, I. V.; Kirmaier, C.; Hindin, E.; Diers, J. R.; Boyle, P. D.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Inorg. Chem. 2003, 42, 6629-6647.
31. Treibs, A.; Kreuzer, F. H. Justus Liebigs Ann. Chem. 1968, 718, 208-223.
32. Vos de Wael, E.; Pardoen, J. A.; Van Koeveringe, J. A.; Lugtenburg, J. Red. Trav. Chim. Pays-Bas 1977, 96, 306-309.
33. Khachatur'yan, A. A.; Evstigneeva, R. P.; Preobrazhenskii, N. A. Zh. Obshch. Khim. 1966, 36, 808-810.
34. Cheng, L.; Ma, J. Synth. Commun. 1994, 24, 2771-2775.
35. Johnson, A. W.; Markham, E.; Price, R.; Shaw, K. B. J. Chem. Soc. 1958, 4254-4257.
36. Paine, J. B., III; Dolphin, D. J. Org. Chem. 1988, 53, 2787-2795.
37. de Groot, J. A.; Gorter-La Roy, G. M.; van Koeveringe, J. A.; Lugtenburg, J. Org. Prep. Proced. Int. 1981, 13, 97-101.
38. Ballantine, J. A.; Jackson, A. H.; Kenner, G. W.; McGillivray, G. Tetrahedron 1966, 241-259.
39. Omote, M.; Ando, A.; Takagi, T.; Koyama, M.; Kumadaki, I. Tetrahedron 1996, 52, 13961-13970.
40. Omote, M.; Ando, A.; Sato, K.; Kumadaki, I. Tetrahedron 2001, 57, 8085-8094.
41. (41 ) Clezy, P. S.; Fookes, C. J. R.; Prashar, J. K. Aust. J. Chem. 1989, 42, 775-786.
42. Treibs, A.; Strell, M.; Strell, I.; Grimm, D. Liebigs Ann. Chem. 1978, 289-305.
43. Falk, H.; Hofer, O.; Lehner, H. Monatsh. Chem. 1974, 105, 169-178.