Photocycloaddition of 2,3-dihydro-2,2-dimethyl-4H-thiopyran-4-one (a 4-thiacyclohex-2-enone) to bona fide triplet quenchers. A contradiction?

Synthesis

Volumn , Issue 9, 2007, Pages 1426-1433

  Margaretha, Paul ^a   Schmidt, Kerstin ^a   Kopf, Jürgen ^a   Sinnwell, Volker ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

1,4 biradicals; 1 chlorocyclobutanecarbonitriles; 2+2 photocycloaddition; Vinylcyclobutanes

Indexed keywords

1,4-BIRADICALS; 1-CHLOROCYCLOBUTANECARBONITRILES; PHOTOCYCLOADDITION; VINYLCYCLOBUTANES;

OLEFINS; PHOTOCHEMICAL REACTIONS; QUENCHING; STEREOCHEMISTRY;

KETONES;

2,3 DIHYDRO 2,2 DIMETHYL 4H THIOPYRAN 4 ONE; 3 CHLOROACRYLONITRILE; ISOPRENE; KETONE DERIVATIVE; MALONONITRILE; NITRILE; PYRAN; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; IRRADIATION; STEREOSPECIFICITY;

EID: 34249087750     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965998     Document Type: Article

References (30)

1. Margaretha, P. In Molecular and Supramolecular Photochemistry, Vol. 12;
2. Griesbeck, A. G.; Mattay, J., Eds.; Marcel Dekker: New York, 2005, 211-238; and references cited therein.
3. Ciamician, G.; Silber, P. Ber. Dtsch. Chem. Ges. 1908, 41, 1928.
4. Valenta, Z.; Liu, H. J. Org. Synth., Coll. Vol. VI; John Wiley & Sons: London, 1988, 1024.
5. Lam, E. Y. Y.; Valentine, D.; Hammond, G. S. J. Am. Chem. Soc. 1967, 89, 3482.
6. Cantrell, T. S. J. Org. Chem. 1974, 39, 3063.
7. Sano, T.; Toda, J.; Tsuda, Y. Chem. Pharm. Bull. 1983, 31, 2960.
8. Demuth, M.; Pandey, B.; Wietfeld, B.; Said, H.; Viader, J. Helv. Chim. Acta 1988, 71, 1392.
9. Sano, T.; Horiguchi, Y.; Tsuda, Y.; Furuhata, K.; Takayanagi, H.; Ogura, H. Chem. Pharm. Bull. 1987, 35, 9.
10. Sano, T.; Enomoto, H.; Kurebayashi, Y.; Horiguchi, Y.; Tsuda, Y. Chem. Pharm. Bull. 1993, 41, 471.
11. Witte, B.; Margaretha, P. Org. Lett. 1999, 1, 173.
12. Witte, B.; Meyer, L.; Margaretha, P. Helv. Chim. Acta 2000, 83, 554.
13. Lohmeyer, B.; Schmidt, K.; Margaretha, P. Helv. Chim. Acta 2006, 89, 854.
14. Schuster, D. I.; Dunn, D. A.; Heibel, G. E.; Brown, P. M.; Rao, J. M.; Woning, J.; Bonneau, R. J. Am. Chem. Soc. 1991, 113, 6245.
15. Broeker, J. L.; Eksterowicz, J. E.; Belk, A. J.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 1847.
16. Moorthy, J. N.; Koner, A. L.; Samantha, S.; Singhal, N.; Nau, W. M.; Weiss, R. G. Chem. Eur. J. 2006, 12, 8744.
17. Plettner, E.; Mohle, A.; Mwangi, M. T.; Griscti, J.; Patrick, B. O.; Nair, R.; Batchelor, R. J.; Einstein, F. Tetrahedron: Asymmetry 2005, 16, 2754.
18. Freeman, P. K.; Balls, D. M.; Brown, D. J. J. Org. Chem. 1968, 33, 2211.
19. Damiano-Gal, J.; Geribaldi, S.; Torri, G.; Rouillard, M.; Azzaro, M. Bull. Soc. Chim. Fr. 1977, 345.
20. Plummer, B. F.; Songster, M. J. Org. Chem. 1990, 55, 1368.
21. Wiberg, K. B.; Barth, D. E.; Pratt, W. E. J. Am. Chem. Soc. 1977, 99, 4286.
22. Schmidt, K.; Kopf, J.; Margaretha, P. Helv. Chim. Acta 2005, 88, 1922.
23. Miller, J. L. J. Phys. Chem. A 2004, 108, 2268.
24. Schuster, D. I.; Heibel, G. E.; Brown, P. B. J. Am. Chem. Soc. 1988, 110, 8261.
25. Lavilla, J. A.; Goodman, J. L. Chem. Phys. Lett. 1987, 141, 149.
26. Schmidt, K.; Kopf, J.; Margaretha, P. Helv. Chim. Acta 2006, 89, 1927.
27. Kosower, E. M.; Sorensen, T. S. J. Org. Chem. 1963, 28, 687.
28. Prajapati, D.; Sandhu, J. S. J. Chem. Soc., Perkin Trans. 1 1993, 739.
29. CCDC-633282 contains the supplementary crystallographic data for 5. This data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request.cif.
30. CCDC-632623 contains the supplementary crystallographic data for 10. This data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request.cif.