Reaction control in synthetic organic photochemistry: Switching between [5+2] and [2+2] Modes of Cycloaddition

Angewandte Chemie - International Edition

Volumn 48, Issue 46, 2009, Pages 8716-8720

  Roscini, Claudio ^a   Cubbage, Kara L ^a   Berry, Malcolm ^b   Orr Ewing, Andrew J ^a   Booker Milburn, Kevin I ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Alkenes; Cycloaddition; Maleimides; Photochemistry; Sensitizers

Indexed keywords

ALKENES; DIRECT IRRADIATION; MALEIMIDES; ORGANIC PHOTOCHEMISTRY; PHOTOCHEMISTRY; PHOTOCYCLOADDITION; REACTION CONDITIONS; REACTION CONTROL; SENSITIZERS; TERT-BUTYLDIMETHYLSILYL;

IRRADIATION; OLEFINS; PHOTOCHEMICAL REACTIONS;

CYCLOADDITION;

ALKENE; AZEPINE DERIVATIVE; CYCLOBUTANE DERIVATIVE; MALEIMIDE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; PHOTOCHEMISTRY; SYNTHESIS;

ALKENES; AZEPINES; CYCLIZATION; CYCLOBUTANES; MALEIMIDES; MOLECULAR STRUCTURE; PHOTOCHEMISTRY;

EID: 70350602256     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200904059     Document Type: Article

References (37)

1. a) K. N. Houk, D. J. Northington, R. E. Duke, J. Am. Chem. Soc. 1972, 94, 6233;
2. b) H. E. Zimmerman, A. C. Pratt, J. Am. Chem. Soc. 1970, 92, 6261;
3. c) H. E. Zimmerman, J. A. Pincock, J. Am. Chem. Soc. 1973, 95, 2951;
4. d) J. S. Swenton, J. A. Hyatt, T. J. Walker, A. L. Crumrine, J. Am. Chem. Soc. 1971, 93, 4808;
5. e) N. J. Turro, Modern Molecular Photochemistry, Benjamin Cummings, California, 1978;
6. f) A. Gilbert, J. Baggot, Essentials of Molecular Photochemistry, Blackwell Scientific, Oxford, 1991.
7. a) L. D. Elliott, M. Berry, A. J. Orr-Ewing, K. I. Booker-Milburn, J. Am. Chem. Soc. 2007, 129, 3078;
8. b) K. B. Eisenthal, N. J. Turro, C. G. Dupuy, D. A. Hrovat, J. Langan, T. A. Jenny, E. V. Sitzmann, J. Phys Chem. 1986, 90, 5168;
9. c) W. G. Dauben, B. Disanayaka, D. J. H. Funhoff, B. E. Kohler, D. E. Schilke, B. Zhou, J. Am. Chem. Soc. 1991, 113, 8367;
10. d) W. G. Dauben, B. Zhou, J. Y. L. Lam, J. Org. Chem. 1997, 62, 9005;
11. e) V. Jakfflbek, A. J. Lees, Inorg. Chem. 2000, 39, 5779.
12. a) R. M. Wilson, K. A. Schnapp, Chem. Rev. 1993, 93, 223;
13. b) E. V. Khoroshilova, N. P. Kuzmina, V. S. Letokhov, Y. A. Matveetz, Appl. Phys. B 1983, 31, 145;
14. c) M. Hara, S. Tojo, T. Majima, J. Phys. Chem. A 2003, 107, 4778;
15. d) N. J. Turro, M. Aikawa, I. R. Gould, J. Am. Chem. Soc. 1982, 104, 856;
16. e) N. J. Turro, M. Aikawa, J. A. Butcher, Jr., G. W. Griffin, J. Am. Chem. Soc. 1980, 102, 5127;
17. f) Y. Kajii, T. Suzuki, Y. Takatori, K. Shibuya, K. Obi, Bull. Chem. Soc. Jpn. 1992, 65, 1349;
18. g) W. C. McGimpsey, J. C. Scaiano, Chem. Phys. Lett. 1987, 138, 13;
19. h) J. Y. Kohno, F. Mafuné, T. Kondow, Bull. Chem. Soc. Jpn. 2005, 78, 957;
20. i) T. I. Sølling, E. W.-G. Diau, C. Kötting, S. de Feyter, A. H. Zewail, ChemPhysChem 2002, 3, 79;
21. j) L. J. Johnston, J. C. Scaiano, J. Am. Chem. Soc. 1987, 109, 5487;
22. k) H. Baumann, C. Merkel, H.-J. Timpe, A. Graness, J. Kleinschmidt, I. R. Gould, N. J. Turro, Chem. Phys. Lett. 1984, 103, 497;
23. l) J. A. Butcher, Jr., H. R. Hinz, N.-h. Tsou, S. Shah, Tetrahedron Lett. 1984, 25, 5483;
24. m) H. Murai, K. Obi, J. Phys. Chem. 1975, 79, 2446.
25. T. Brixer, G. Gerber, ChemPhysChem 2003, 4, 418.
26. C. Roscini, D. M. E. Davis, M. Berry, A. J. Orr-Ewing, K. I. Booker-Milburn, Angew. Chem. 2008, 120, 2315-2318;
27. Angew. Chem. Int. Ed. 2008, 47, 2283.
28. a) K. I. Booker, K. Cowell, A. Sharpe, F. D. Jimenez, Chem. Commun. 1996, 249;
29. b) K. I. Booker-Milburn, S. Gluten, A. Sharpe, Chem. Commun. 1997, 1385;
30. c) K. I. Booker-Milburn, J. K. Cowell, F. D. Jimenez, A. Sharpe, A. J. White, Tetrahedron 1999, 55, 5875.
31. a) K. I. Booker-Milburn, N. J. Costin, R. F. Dainty, D. Patel, A. Sharpe, Tetrahedron Lett. 1998, 39, 7423;
32. b) K. I. BookerMilburn, C. E. Anson, C. Clissold, N. J. Costin, R. F. Dainty, M. Murray, D. Patel, A. Sharpe, Eur. J. Org. Chem. 2001, 1473.
33. a) M. D. Lainchbury, M. I. Medley, P. M. Taylor, P. Hirst, W. Dohle, K. I. Booker-Milburn, J. Org. Chem. 2008, 73, 6497;
34. b) K. I. Booker-Milburn, L. F. Dudin, C. E. Anson, S. D. Guile, Org. Lett. 2001, 3, 3005.
35. D. Davies, C. Murray, M. Berry, A. J. Orr-Ewing, K. I. BookerMilburn, J. Org. Chem. 2006, 72, 1449.
36. -1); from S. L. Murov, I. Carmichael, G. L. Hug, Handbook of Photochemistry, Marcel Dekker, New York, 1993, pp. 56-97.
37. CCDC 739183 (12) contains 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.