Photolysis of chiral 1-pyrazolines to cyclopropanes: Mechanism and stereospecificity

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4906-4911

  Muray, Elena ^a   Illa, Ona ^a   Castillo, José A ^a   Álvarez Larena, Ángel ^a   Bourdelande, José L ^a   Branchadell, Vicenç ^a   Ortuño, Rosa M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; LASER APPLICATIONS; PROPANE; QUENCHING; RATE CONSTANTS; STEREOCHEMISTRY;

PHOTODENITROGENATION;

PHOTOLYSIS;

1 PYRAZOLINE DERIVATIVE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; NITROGEN; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; LASER; PHOTOLYSIS; PHOTOSENSITIZATION; ROTATION; STEREOSPECIFICITY;

EID: 0038616414     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0342471     Document Type: Article

References (46)

1. Smith, M. B.; March, J. Advanced Organic Chemistry, 5th ed.; J. Wiley & Sons: New York, 2001; p 1353 and references therein.
2. For some representative works, see: (a) Engel, P. S.; Shen, L. Can. J. Chem. 1974, 52, 4040. (b) Engel, P. S.; Steel, C. Acc. Chem. Res. Chem. 1973, 6, 275. (c) Engel, P. S.; Nalepa, C. L. Pure Appl. Chem. 1980, 52, 2621. (d) Doubleday, C.; McIver, J. W.; Page, M. J. Am. Chem. Soc. 1982, 104, 6533. (e) Karatsu, T.; Hotta, H.; Kitamura, A. J. Chem. Soc., Chem. Commun. 1991, 1451.
3. For some representative works, see: (a) Engel, P. S.; Shen, L. Can. J. Chem. 1974, 52, 4040. (b) Engel, P. S.; Steel, C. Acc. Chem. Res. Chem. 1973, 6, 275. (c) Engel, P. S.; Nalepa, C. L. Pure Appl. Chem. 1980, 52, 2621. (d) Doubleday, C.; McIver, J. W.; Page, M. J. Am. Chem. Soc. 1982, 104, 6533. (e) Karatsu, T.; Hotta, H.; Kitamura, A. J. Chem. Soc., Chem. Commun. 1991, 1451.
4. For some representative works, see: (a) Engel, P. S.; Shen, L. Can. J. Chem. 1974, 52, 4040. (b) Engel, P. S.; Steel, C. Acc. Chem. Res. Chem. 1973, 6, 275. (c) Engel, P. S.; Nalepa, C. L. Pure Appl. Chem. 1980, 52, 2621. (d) Doubleday, C.; McIver, J. W.; Page, M. J. Am. Chem. Soc. 1982, 104, 6533. (e) Karatsu, T.; Hotta, H.; Kitamura, A. J. Chem. Soc., Chem. Commun. 1991, 1451.
5. For some representative works, see: (a) Engel, P. S.; Shen, L. Can. J. Chem. 1974, 52, 4040. (b) Engel, P. S.; Steel, C. Acc. Chem. Res. Chem. 1973, 6, 275. (c) Engel, P. S.; Nalepa, C. L. Pure Appl. Chem. 1980, 52, 2621. (d) Doubleday, C.; McIver, J. W.; Page, M. J. Am. Chem. Soc. 1982, 104, 6533. (e) Karatsu, T.; Hotta, H.; Kitamura, A. J. Chem. Soc., Chem. Commun. 1991, 1451.
6. For some representative works, see: (a) Engel, P. S.; Shen, L. Can. J. Chem. 1974, 52, 4040. (b) Engel, P. S.; Steel, C. Acc. Chem. Res. Chem. 1973, 6, 275. (c) Engel, P. S.; Nalepa, C. L. Pure Appl. Chem. 1980, 52, 2621. (d) Doubleday, C.; McIver, J. W.; Page, M. J. Am. Chem. Soc. 1982, 104, 6533. (e) Karatsu, T.; Hotta, H.; Kitamura, A. J. Chem. Soc., Chem. Commun. 1991, 1451.
7. (a) Wilkinson, F.; Kelly, G. P. J. Photochem. Photobiol., A: Chem. 1990, 52, 309.
8. (b) Wilkinson, F.; Kelly, G. P.; Michael, C. J. Photochem. Photobiol., A: Chem. 1990, 52, 309.
9. (c) Blair, J. T.; Sahyun, M. R. V.; Sharma, D. K. J. Photochem. Photobiol., A: Chem. 1994, 77, 133.
10. (a) Adam, W.; Grabowski, S. J. Am. Chem. Soc. 1987, 109, 7572.
11. (b) Adam, W.; García, H.; Marti, V.; Moorthy, J. N. J. Am. Chem. Soc. 1999, 121, 9475.
12. (c) Adam, W.; Martí, V.; Sahin, C.; Trofimov, A. J. Am. Chem. Soc. 2000, 122, 5002.
13. Adam, W.; Bottle, S. E.; Finzel, R.; Kammel, T.; Peters, E.-M.; Peters, K.; von Schnering, H. G.; Walz, L. J. Org. Chem. 1992, 57, 982.
14. (a) Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629.
15. (b) Beckwith, A. L. J.; Bowry, V. W. J. Org. Chem. 1988, 53, 1632.
16. (c) Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983.
17. (d) Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992.
18. Robertson, M. J.; Simons, J. J. Phys. Chem. 1997, 101, 2379.
19. Yamamoto, N.; Olivucci, M.; Celani, P.; Bernardi, F.; Robb, M. A. J. Am. Chem. Soc. 1998, 120, 2391.
20. Muray, E.; Álvarez-Larena, A.; Piniella, J. F.; Branchadell, V.; Ortuño, R. M. J. Org. Chem. 2000, 65, 388.
21. Moglioni, A. G.; Garcia-Expósito, E.; Alvarez-Larena, A.; Branchadell, V.; Moltrasio, G. Y.; Ortuño, R. M. Tetrahedron: Asymmetry 2000, 11, 4903.
22. Illa, O.; Muray, E.; Amsallem, D.; Moglioni, A. G.; Gornitzka, H.; Branchadell, V.; Baceiredo, A.; Ortuño, R. M. Tetrahedron: Asymmetry, 2002, 13, 2593.
23. (a) Jiménez, J. M.; Rifé, J.; Ortuño, R. M. Tetrahedron: Asymmetry, 1996, 7, 537.
24. (b) Jiménez, J. M.; Ortuño, R. M. Tetrahedron: Asymmetry, 1996, 7, 3203.
25. (c) Rifé, J.; Lajoie, G. A.; Ortuño, R. M. J. Org. Chem. 1999, 64, 8958.
26. (d) Illescas, B.; Rifé, J.; Ortuño, R. M.; Martín, N. J. Org. Chem. 2000, 65, 6246.
27. (a) Díaz, M.; Jiménez, J. M.; Ortuño, R. M. Tetrahedron: Asymmetry, 1997, 8, 2465.
28. (b) Martín-Vilà, M.; Muray, E. Aguado, G. P.; Alvarez-Larena, A.; Branchadell, V.; Minguillón, C.; Giralt, E.; Ortuño, R. M. Tetrahedron: Asymm. 2000, 11, 3569.
29. Rifé, J.; Ortuño, R. M. Tetrahedron: Asymmetry 1999, 10, 4245.
30. Muray, E.; Rifé, J.; Branchadell, V.; Ortuño, R. M. J. Org. Chem. 2002, 67, 4520.
31. Jiménez, J. M.; Bourdelande, J. L.; Ortuño, R. M. Tetrahedron 1997, 53, 3777.
32. García-Expósito, E.; Bearpark, M. J.; Ortuño, R. M.; Branchadell, V.; Robb, M. A.; Wilsey, S. J. Org. Chem. 2001, 66, 8811.
33. (a) Furlani, T. R.; King, H. F. J. Phys. Chem. 1985, 82, 5577.
34. (b) Carlacci, L.; Doubleday: C. Jr.; Furlani, T. R.; King, H. F.; McIver, J. W., Jr. J. Am. Chem. Soc. 1987, 109, 5323.
35. Carey, M. EPA Newsletter 1994, 52, 21.
36. Gaussian 98, Revision A.7: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A,; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1998. http://www.gaussian.com.
37. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
38. (a) Wang, Y.; Perdew, J. P. Phys. Rev. B 1991, 44, 13298.
39. (b) Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Phys. Rev. B 1992, 46, 6671.
40. (a) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
41. (b) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
42. (c) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
43. Roos, B. O. Adv. Chem. Phys. 1987, 69, 63.
44. (a) Ragazos, I. N.; Robb, M. A.; Bernardi, F.; Olivucci, M. Chem. Phys. Lett. 1992, 197, 217.
45. (b) Bearpark, M. J.; Robb, M. A.; Schlegel, H. B. Chem. Phys. Lett. 1994, 223, 269.
46. Koseki, S.; Schmidt, M. W.; Gordon, M. S. J. Phys. Chem. 1992, 96, 10768.