Photochemical rearrangements of norbornadiene Pauson-Khand cycloadducts

Angewandte Chemie - International Edition

Volumn 46, Issue 31, 2007, Pages 5943-5946

  Lledó, Agustí ^a   Benet Buchholz, Jordi ^b   Solé, Albert ^c   Olivella, Santiago ^d   Verdaguer, Xavier ^a   Riera, Antoni ^a  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

^d DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

Cycloaddition; Photochemistry; Radical reactions; Rearrangement; Synthetic methods

Indexed keywords

OLEFINS; PHOTOCHEMICAL REACTIONS;

RADICAL REACTIONS; SYNTHETIC METHODS;

CYCLOADDITION;

EID: 34547781285     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701658     Document Type: Article

References (48)

1. Selected reviews: a) J. Blanco-Urgoiti, L. Anorbe, L. Perez-Serrano, G. Dominguez, J. Perez-Castells, Chem. Soc. Rev. 2004, 33, 32;
2. b) S. E. Gibson (née Thomas), A. Stevenazzi, Angew. Chem. 2003, 115, 1844;
3. Angew. Chem. Int. Ed. 2003, 42, 1800;
4. c) K. M. Brummond, J. L. Kent, Tetrahedron 2000, 56, 3263;
5. d) Y. Keun Chung, Coord. Chem. Rev. 1999, 188, 297;
6. e) S. L. Buchwald, F. A. Hicks in Comprehensive Asymmetric Catalysis I-III, 1999, pp. 491-510;
7. f) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, pp. 1037-1064.
8. V. Bernardes, N. Kann, A. Riera, A. Moyano, M. A. Pericàs, A. E. Greene, J. Org. Chem. 1995, 60, 6670.
9. a) X. Verdaguer, A. Moyano, M. A. Pericàs, A. Riera, M. A. Maestro, J. Mahia, J. Am. Chem. Soc. 2000, 122, 10242;
10. b) X. Verdaguer, M. A. Pericàs, A. Riera, M. A. Maestro, J. Mahia, Organometallics 2003, 22, 1868;
11. c) X. Verdaguer, A. Lledo, C. Lopez-Mosquera, M. A. Maestro, M. A. Pericàs, A. Riera, J. Org. Chem. 2004, 69, 8053;
12. d) J. Solà, M. Revés, A. Riera, X. Verdaguer, Angew. Chem. 2007, 119, 5108;
13. Angew. Chem. Int. Ed. 2007, 46, 5020.
14. a) W. H. Horspool, Photochemistry 2004, 35, 17;
15. b) W. M. Horspool, Photochemistry 2003, 34, 29;
16. c) D. I. Schuster, CRC Handbook of Organic Photochemistry and Photobiology, 2nd Ed., CRC Press, Boca Raton, 2004, pp. 72/71-72/24.
17. I. Marchueta, S. Olivella, L. Solà, A. Moyano, M. A. Pericàs, A. Riera, Org. Lett. 2001, 3, 3197.
18. I. Gomez, S. Olivella, M. Reguero, A. Riera, A. Sole, J. Am. Chem. Soc. 2002, 124, 15375.
19. a) Z. Benko, B. Fraser-Reid, P. S. Mariano, A. L. J. Beckwith, J. Org. Chem. 1988, 53, 2066;
20. b) B. Fraser-Reid, N. L. Holder, D. R. Hicks, D. L. Walker, Can. J. Chem. 1977, 55, 3978.
21. a) N. Mase, Y. Watanabe, T. Toru, Bull. Chem. Soc. Jpn. 1998, 71, 2957;
22. b) D. I. Schuster, J.-M. Yang, J. Woning, T. A. Rhodes, A. W. Jensen, Can. J. Chem. 1995, 73, 2004;
23. c) J. Wang, A. Gossauer, Helv. Chim. Acta 1994, 77, 533.
24. CCDC-646970 and -646971 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
25. As an alternative to the standard Rayonet apparatus with 16 lamps (8 W, 350 nm), a simple home made apparatus equipped with eight lamps (Philips, TL 8W/08 FAM, 365 nm) was used.
26. F. B. Mallory, C. S. Wood, J. T. Gordon, J. Am. Chem. Soc. 1964, 86, 3094.
27. Some recent examples: a) S. Amin, J. Camanzo, K. Huie, S. S. Hecht, J. Org. Chem. 1984, 49, 381;
28. b) P. H. Gore, F. S. Kamonah, Synthesis 1978, 773;
29. c) E. Martínez, J. C. Estévez, R. J. Estévez, L. Castedo, Tetrahedron 2001, 57, 1981.
30. Selected synthetic applications of endo-cyclopentadien-1,8-diones: a) G. Mehta, S. S. Ramesh, Can. J. Chem. 2005, 83, 581;
31. b) G. Mehta, R. S. Kumaran, Tetrahedron Lett. 2001, 42, 8097;
32. c) G. Mehta, D. S. Reddy, J. Chem. Soc. Perkin Trans. 1 2001, 1153;
33. d) P. Francis Schuda, M. R. Heimann, Tetrahedron 1984, 40, 2365;
34. e) L. A. Paquette, R. F. Daivs, D. R. James, Tetrahedron Lett. 1974, 15, 1615;
35. f) E. Vogel, E. G. Wyes, Chem. Ber. 1965, 98, 3680;
36. g) R. C. Cookson, N. S. Isaacs, M. Szelke, Tetrahedron 1964, 20, 717.
37. a) P. Quadrelli, S. Romano, L. Toma, P. Caramella, J. Org. Chem. 2003, 68, 6035;
38. b) G. Mehta, S. H. K. Reddy, Synlett 1993, 75;
39. c) G. Mehta, S. H. K. Reddy, Tetrahedron Lett. 1991, 32, 6403;
40. d) P. E. Eaton, S. A. Cerefice, J. Chem. Soc. Chem. Commun. 1970, 1494.
41. a) C. J. Baker, G. I. Fray, G. R. Geen, K. Ryan, J. Chem. Soc. Perkin Trans. 1 1994, 793;
42. b) J. Zhu, A. J. H. Klunder, B. Zwanenburg, Tetrahedron Lett. 1993, 34, 3335;
43. c) A. P. Marchand, P. W. Jin, J. L. Flippen-Anderson, R. Gilardi, C. George, J. Chem. Soc. Chem. Commun. 1987, 1108;
44. d) B. Fuchs, M. Pasternak, B. Pazhenchevsky, J. Org. Chem. 1981, 46, 2017;
45. e) R. C. Cookson, J. Hudec, R. O. Williams, Tetrahedron Lett. 1960, 1, 29.
46. a) G. Maier, S. Senger, J. Am. Chem. Soc. 1997, 119, 5857;
47. b) P. Caramella, P. Quadrelli, L. Toma, S. Romano, K. S. Khuong, B. Nortrop, K. N. Houk, J. Org. Chem. 2005, 70, 2994.
48. A related bond scission affording two allyl radicals was postulated in the isomerization of 5-(cyclopent-2-en-1-yl)-2,5-dihydro-1H-pyrrol-2- ones: M. N. Wrobel, P. Margaretha, Chem. Commun. 1998, 541.