The photochemistry of 4-azidopyridine-1-oxide

Journal of Organic Chemistry

Volumn 71, Issue 24, 2006, Pages 9023-9029

  Hostetler, Katherine J ^a   Crabtree, Kyle N ^a   Poole, James S ^a  

^a BALL STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN COMPOUNDS;

CYCLIZATION; SPIN DENSITY;

PHOTOLYSIS;

4 AZIDOPYRIDINE 1 OXIDE; AZEPINE DERIVATIVE; AZIDE; AZIRINE DERIVATIVE; NITRENE; NITROGEN DERIVATIVE; PYRIDINE 1 OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; LASER; ORGANIC CHEMISTRY; PHOTOCHEMISTRY; PHOTOLYSIS; STRUCTURE ANALYSIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; KINETICS; OXIDES; PHOTOCHEMISTRY; PYRIDINES; SPECTROPHOTOMETRY, INFRARED;

EID: 33751556643     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061259o     Document Type: Article

References (38)

1. Itai, T.; Kamiya, S. Chem. Pharm. Bull. 1961, 9, 87.
2. (a) Itai, T.; Kamiya, S. Chem. Pharm. Bull. 1963, 11, 348.
3. (b) Itai, T.; Kamiya, S. Chem. Pharm. Bull. 1963, 11, 1059.
4. Abramovitch, R. A.; Bachowska, B.; Tomasik, P. Pol. J. Chem. 1984, 58, 805.
5. Abramovitch, R. A.; Cue, B. W., Jr. J. Org. Chem. 1973, 38, 173.
6. (b) Abramovitch, R. A.; Cue, B. W., Jr. J. Am. Chem. Soc. 1976, 98, 1478.
7. Platz, M. S. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S. Jones, M. J., Eds.; John Wiley & Sons Inc.: Hoboken, NJ, 2004; pp 522-545.
8. (b) Borden, W. T.; Gritsan, N. P.; Hadad, C. M.; Karney, W. L.; Kemnitz, C. R.; Platz, M. S. Acc. Chem. Res. 2000, 33, 765.
9. (c) Gritsan, N. P.; Zhu, Z.; Hadad, C. M.; Platz, M. S. J. Am. Chem. Soc. 1999, 121, 1202.
10. Gritsan, N. P.; Likhotvoric, I.; Tsao, M.-L.; Celibi, N.; Platz, M. S.; Karney, W. L.; Kemnitz, C. R.; Borden, W. T. J. Am. Chem. Soc. 2001, 123, 1425.
11. (b) Gritsan, N. P.; Tigelaar, D.; Platz, M. S. J. Phys. Chem. A 1999, 103, 4465.
12. Leyshon, L. J.; Reiser, A. J. Chem. Soc., Faraday Trans. 2, 1972, 1918.
13. (b) Go, C. L.; Waddell, W. H. J. Org. Chem. 1983, 48, 2897.
14. Katritzky, A. R. J. Chem. Soc. Abstr. 1956, 2404.
15. For example, see Martin, C. B.; Shi, X.; Tsao, M.-L.; Karweik, D.; Brooke, J.; Hadad, C. M.; Platz, M. S.; J. Phys. Chem. B 2002, 106, 10263. Temperature control was achieved by utilizing the quartz cryostat/ thermostabilized nitrogen stream system described in ref 5c.
16. For example, see: Martin, C. B.; Tsao, M-L.; Hadad, C. M.; Platz, M. J. J. Am. Chem. Soc. 2002, 125, 7226.
17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; Gaussian 03, Revision C.02: Gaussian. Inc.: Wallingford, CT, 2004.
18. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
19. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
20. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
21. Scott, A. P.; Radom, L. J. Phvs. Chem. 1996, 100, 16502.
22. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
23. (b) Reed, A. E.; Weinhold, F.; Curtiss, J. A. Chem. Rev. 1988, 88, 899.
24. (a) Karney, W. L.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 1378.
25. (b) Johnson, W. T. G.; Sullivan, M. B.; Cramer, C. J. Int. J. Quantum Chem. 2001, 85, 492.
26. Cerro-Lopez, M.; Gritsan, N. P.; Zhu, Z.; Platz, M. S. J. Phys. Chem. A 2000, 104, 9681.
27. Marcinek, A.; Leyva, E.; Whitt, D.; Platz, M. S. J. Am. Chem. Soc. 1993, 115, 8609.
28. (a) DeGraff, B. A.; Gillespie, D. W.; Sundberg, R. J. J. Am. Chem. Soc. 1974, 96, 7491.
29. (b) Li, Y.-Z.; Kirby, J. P.; George, M. W.; Poliakoff, M.; Schuster, G. B. J. Am. Chem. Soc. 1998, 110, 8092.
30. Muniz-Miranda, M.; Pergolese, B.; Sbrana, G.; Bigotto, A. J. Mol. Struct. 2005, 744-747, 339.
31. (a) Albini, A.; Alpegiani, M. Chem. Rev. 1984, 84, 43.
32. (b) Shi, X.; Poole, J. S.; Emenike, I.; Burdzinski, G.; Platz, M. S. J. Phys. Chem. A 2005, 109, 1491.
33. Gritsan, N. P.; Gudmundsdottir, A. D.; Tigelar, D.; Platz, M. S. J. Phys. Chem. A 1999, 103, 3458.
34. (a) Lebvedev, Y. A.; Rosantzev, E. G.; Kalashnikova, L. A.; Lebvedev, V. P.; Neiman, M. B.; Apin, A. Y. Dokl. Akad. Nauk SSSR (Engl. Trans.) 1966, 40, 460.
35. (b) Lebvedev, Y. A.; Rosantzev, E. G.; Neiman, M. B.; Apin, A. Y. Dokl. Akad. Nauk SSSR (Engl. Trans.) 1966, 40, 460.
36. (c) Mahoney, L. R.; Mendenhall, G. D; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 8610.
37. Pietrzycki, W.; Tomasik, P. Pol. J. Chem. 1998, 72, 893.
38. 1SC may be increased three orders of magnitude with appropriate π-donor substituents (ref 6b).