Ring contraction of bridgehead sultams by photoinduced di-π-methane rearrangement

Journal of Organic Chemistry

Volumn 71, Issue 6, 2006, Pages 2456-2459

  Dura, Robert D ^a   Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BENZENE; BONDING; DERIVATIVES; METHANE; RADIATION; SOLUTIONS; VINYL RESINS;

BRIDGEHEAD SULTAMS; ELECTRONIC REBONDING PATHWAY; PARENT SYSTEM; PHOTOINDUCED DI-Π-METHANE REARRANGEMENT; REGIOSPECIFICITY; TETRACYCLIC SULTAM; TRIPLET-SENSITIZED IRRADIATION;

PHOTOCHEMICAL REACTIONS;

8 THIA 9 AZATRICYCLO[7.2.1.0 2,7]DODECA 2,4,6,10 TETRAENE; ACETONE; METHANE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; IRRADIATION; ISOMERIZATION; LIGHT; PHOTOCHEMISTRY; SYNTHESIS;

EID: 33645029431     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0526587     Document Type: Article

References (28)

1. (a) Beddoes, R. L.; Dalton, L.; Joule, J. A.; Miller, O. S.; Street, J. D.; Watt, C. I. F. J. Chem. Soc., Perkin Trans. 2 1986, 787.
2. (b) For additional examples, see: Klug, H. P. Acta Crystallogr. 1968, 24, 792.
3. (c) Oppolzer, W.; Rodriguez, I.; Starkmann, C.; Walther, E. Tetrahedron Lett. 1990, 31, 5019.
4. (a) Dauben, P.; Dodd, R. H. Org. Lett. 2000, 2, 2327.
5. (b) Liang, J.-L.; Yuan, S.-X.; Chang, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 4507.
6. Paquette, L. A.; Barton, W. R. S.; Gallucci, J. C. Org. Lett. 2004, 6, 1313.
7. Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96, 3065 and references therein.
8. Paquette, L. A.; Meisinger, R. H. Tetrahedron Lett. 1970, 1469.
9. (a) Paquette, L. A.; Coghlan, M. J.; Cottrell, C. E.; Irie, T.; Tanida, H. J. Org. Chem. 1986, 51, 696.
10. (b) Paquette, L. A.; Burke, L. D.; Irie, T.; Tanida, H. J. Org. Chem. 1987, 52, 3246.
11. (a) Grigg, R.; Santhakumar, V.; Sridharan, V.; Stevenson, P.; Teasdale, A.; Thornton-Pett, M.; Worakun, T. Tetrahedron 1991, 49, 9703.
12. (b) Grigg, R.; Sridharan, V.; York, M. Tetrahedron Lett. 1998, 39, 4139.
13. (c) Grigg, R.; York, M. Tetrahedron Lett. 2000, 41, 7255.
14. Evans, P.; McCabe, T.; Morgon, B.; Reau, S. Org. Lett. 2005, 7, 43.
15. Paquette, L. A.; Schloss, J.; Efremov, I.; Fabris, F.; Gallou, F.; Mendez-Andino, J.; Yang, J. Org. Lett. 2000, 2, 1259.
16. The triplet-sensitized photoisomerization of benzonorbornadienes carrying substituents at the bridgehead positions and vinyl segments has been thoroughly scrutinized: (a) Paquette, L. A.; Ku, A. Y.; Santiago, C.; Rozeboom, M. D.; Houk, K. N. J. Am. Chem. Soc. 1979, 101, 5972.
17. (b) Ku, A. Y.; Paquette, L. A.; Rozeboom, M. D.; Houk, K. N. J. Am. Chem. Soc. 1979, 101, 5981.
18. (c) Paquette, L. A.; Bay, E.; Ku, A. Y.; Rondan, N. G.; Houk, N. K. J. Org. Chem. 1982, 47, 422.
19. (d) Paquette, L. A.; Bay, E. J. Org. Chem. 1982, 47, 4597.
20. (e) Paquette, L. A.; Bay, E. J. Am. Chem. Soc. 1984, 106, 6693.
21. (f) Paquette, L. A.; Varadarajan, A.; Bay, E. J. Am. Chem. Soc. 1984, 106, 6702.
22. Full consideration has also been given to the control of benzo-vinyl bonding options by aryl-bound functionality: (a) Paquette, L. A.; Cottrell, D. M.; Snow, R. A.; Gifkins, K. B.; Clardy, J. J. Am. Chem. Soc. 1975, 97, 3275.
23. (b) Santiago, C.; Houk, K. N.; Snow, R. A.; Paquette, L. A. J. Am. Chem. Soc. 1976, 98, 7443.
24. (c) Paquette, L. A.; Cottrell, D. M.; Snow, R. A. J. Am. Chem. Soc. 1977, 99, 3723.
25. (d) Snow, R. A.; Cottrell, D. M.; Paquette, L. A. J. Am. Chem. Soc. 1977, 99, 3734.
26. (e) Santiago, C.; McAlduff, E. J.; Houk, K. N.; Snow, R. A.; Paquette, L. A. J. Am. Chem. Soc. 1978, 100, 6149.
27. (f) Paquette, L. A.; Burke, L. D. J. Org. Chem. 1987, 52, 2674.
28. Lane, J. W.; Holcomb, R. L. Org. Lett. 2003, 5, 4017.