[2+2] Photocycloaddition of 2(5 H)-Furanone to unsaturated compounds. Insights from first principles calculations and transient-absorption measurements

Journal of Organic Chemistry

Volumn 75, Issue 13, 2010, Pages 4392-4401

  Cucarull Gonzalez J R ^a   Hernando, J ^a   Alibes R ^a   Figueredo, M ^a   Font, J ^a   Rodriguez Santiago L ^a   Sodupe, M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2(5H)-FURANONE; [2 + 2] PHOTOCYCLOADDITION; ABSORPTION MEASUREMENTS; CAS-SCF; CYCLOBUTANES; ENERGY PATHS; FIRST-PRINCIPLES CALCULATION; PHOTOCHEMICAL ADDITION; SYNTHETIC CONDITIONS; TRIPLET STATE; TRIPLET SURFACES;

ACETYLENE; BUTANE; CHEMICAL DETECTION; ETHYLENE; LIGHTING; UNSATURATED COMPOUNDS;

REACTION INTERMEDIATES;

ACETYLENE; ALKENE; CYCLOBUTANE; ETHYLENE; FURANONE DERIVATIVE; LACTONE;

ABSORPTION; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CYCLOADDITION; PHOTOCHEMISTRY; SENSITIZATION;

4-BUTYROLACTONE; ABSORPTION; ALKENES; CYCLIZATION; ETHYLENES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; QUANTUM THEORY; STEREOISOMERISM;

EID: 77954123421     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100341a     Document Type: Article

References (57)

1. Corey, E. J.; Bass, J. D.; LeMahieu, R.; Mitra, R. B. J. Am. Chem. Soc. 1964, 86, 5570
2. Baldwin, S. W. In Organic Photochemistry; Padwa, A., Ed.; Marcel Dekker: New York, 1981; p 123.
3. Crimmins, M. T. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5, p 123
4. Demuth, M.; Mikhail, G. Synthesis 1989, 145
5. Bach, T. Synthesis 1998, 683
6. Namyslo, J. C.; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485
7. Iriondo-Alberdi, J.; Greaney, M. F. Eur. J. Org. Chem. 2007, 4801
8. Alibes, R.; Bourdelande, J. L.; Font, J.; Parella, T. Tetrahedron 1996, 52, 1279
9. de March, P.; Figueredo, M.; Font, J.; Raya, J.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 2003, 68, 2437
10. Alibes, R.; De March, P.; Figueredo, M.; Font, J.; Racamonde, M.; Parella, T. Org. Lett. 2004, 6, 1449
11. Racamonde, M.; Alibes, R.; Figueredo, M.; Font, J.; de March, P. J. Org. Chem. 2008, 73, 5944
12. Alibes, R.; Alvarez-Larena, A.; de March, P.; Figueredo, M.; Font, J.; Parella, T.; Rustullet, A. Org. Lett. 2006, 8, 491
13. Rustullet, A.; Alibes, R.; De March, P.; Figueredo, M.; Font, J. Org. Lett. 2007, 9, 2827
14. Maradyn, D. J.; Weedon, A. C. Tetrahedron Lett. 1994, 35, 8107
15. Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3
16. Shen, R.; Corey, E. J. Org. Lett. 2007, 9, 1057
17. Yamauchi, S.; Hirota, N.; Higuchi, J. J. Phys. Chem. 1988, 92, 2129
18. Schuster, D. I.; Heibel, G. E.; Caldwell, R. A.; Tang, W. Photochem. Photobiol. 1990, 52, 645
19. Schuster, D. I.; Dunn, D. A.; Heibel, G. E.; Brown, P. B.; Rao, J. M.; Woning, J.; Bonneau, R. J. Am. Chem. Soc. 1991, 113, 6245
20. Bertrand, C.; Bouquant, J.; Pete, J. P.; Humbel, S. THEOCHEM 2001, 538, 165
21. Wilsey, S.; Gonzalez, L.; Robb, M. A.; Houk, K. N. J. Am. Chem. Soc. 2000, 122, 5866
22. Garcia-Exposito, E.; Bearpark, M. J.; Ortuno, R. M.; Robb, M. A.; Branchadell, V. J. Org. Chem. 2002, 67, 6070
23. Arnaut, L. G.; Caldwell, R. A.; Elbert, J. E.; Melton, L. A. Rev. Sci. Instrum. 1992, 63, 5381
24. Flechtner, T. W. J. Org. Chem. 1977, 42, 901
25. Ohga, K.; Matsuo, T. Bull. Chem. Soc. Jpn. 1970, 43, 3505
26. Tada, M.; Kokubo, T.; Sato, T. Tetrahedron 1972, 28, 2121
27. Kosugi, H.; Sekiguchi, S.; Sekita, R.; Uda, H. Bull. Chem. Soc. Jpn. 1976, 49, 520
28. Koch, W.; Holthausen, M. C. A Chemists Guide to Density Functional Theory, 2 nd ed.; Wiley: Weinheim, 2001.
29. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2008, 4, 1849
30. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157
31. Gil, A.; Simon, S.; Rodriguez-Santiago, L.; Bertran, J.; Sodupe, M. J. Chem. Theory Comput. 2007, 3, 2210
32. Rodriguez-Santiago, L.; Sodupe, M.; Oliva, A.; Bertran, J. J. Am. Chem. Soc. 1999, 121, 8882
33. Rodriguez-Santiago, L.; Sodupe, M.; Oliva, A.; Bertran, J. J. Phys. Chem. A 2000, 104, 1256
34. Hemelsoet, K.; Moran, D.; Van Speybroeck, V.; Waroquier, M.; Radom, L. J. Phys. Chem. A 2006, 110, 8942
35. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
36. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
37. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623
38. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 6908
39. Roos, B. O. Adv. Chem. Phys. 1987, 69, 63
40. Bartlett, R. J. Annu. Rev. Phys. Chem. 1981, 32, 359
41. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. Chem. Phys. Lett. 1989, 157, 479
42. Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036
43. 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.; Rev. C. 02 ed.; Gaussian Inc.: Pittsburgh PA, 2003.
44. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899
45. Weinhold, F.; Carpenter, J. E. The Structure of Small Molecules and Ions; Plenum: New York, 1988.
46. Lang, K.; Bezdicka, P.; Bourdelande, J. L.; Hernando, J.; Jirka, I.; Kafunkova, E.; Kovanda, F.; Kubat, P.; Mosinger, J.; Wagnerova, D. M. Chem. Mater. 2007, 19, 3822
47. Caldwell, R. A.; Cao, C. V. J. Am. Chem. Soc. 1982, 104, 6174
48. Platt, J. R.; Price, W. C. J. Chem. Phys. 1949, 17, 466
49. Porter, G.; Dunston, J. M.; Cessna, A. J.; Sugamori, S. E. J. Chem. Soc., Faraday Trans. 1971, 67, 3149
50. 1H NMR signals of a saturated solution of ethylene in acetonitrile (s = 0.029 M).
51. Stern, O.; Volmer, M. Physik. Z. 1919, 20, 183
52. Kochevar, I. H.; Wagner, P. J. J. Am. Chem. Soc. 1970, 92, 5742
53. Miyuki, H.; Hidemasa, O.; Tsukasa, K.; Tsutomu, K. J. Polym. Sci., Part A: Polym. Chem. 1970, 8, 3295
54. Although the transient absorption of 2(5 H)-furanone triplet state in acetone is found to peak at ∼360 nm, this species gives rise to a residual absorption signal at 302 nm, whose intensity is much lower than that of ethylene triplet state but rises with increasing concentration of 2(5 H)-furanone until a significant contribution to the overall decay trace is displayed at this wavelength. It is important to note that 2(5 H)-furanone triplet state may be generated both by direct absorption of the lactone at 266 nm and sensitization via ethylene triplet state.
55. Kelly, J. F. D.; Kelly, J. M.; McMurry, T. B. H. J. Chem. Soc., Perkin Trans. 2 1999, 1933
56. Ahmed, M.; Peterka, D. S.; Suits, A. G. J. Chem. Phys. 1999, 110, 4248
57. Qi, F.; Sorkhabi, O.; Suits, A. G. J. Chem. Phys. 2000, 112, 10707