New photorearrangements of 2-cyclopentenones. The genesis and fate of cyclopropylcarbinyl biradical intermediates [1]

Journal of the American Chemical Society

Volumn 122, Issue 7, 2000, Pages 1540-1541

  Paquette, Leo A ^a   Zhao, Zhong ^a   Gallou, Fabrice ^a   Liu, Jian ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ALKENE; CYCLOPENTENONE; CYCLOPROPANE DERIVATIVE; RADICAL;

CHEMICAL BOND; CYCLIZATION; ISOMERISM; LETTER; PHOTOCHEMISTRY; REACTION ANALYSIS; ULTRAVIOLET RADIATION;

EID: 0034005284     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994081e     Document Type: Letter

References (28)

1. Eaton, P. E. J. Am. Chem. Soc. 1962, 84, 2344.
2. (a) Eaton, P. E.; Hurt, W. S. J. Am. Chem. Soc. 1966, 88, 5038.
3. (b) For a recent review, consult: Schuster, D. I.; Lem, G.; Kaprinidis, N. A. Chem. Rev. 1993, 93, 3.
4. Select reviews: (a) Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
5. (b) Crimmins, M. T.; Reinhold, T. L. Org. React. (NY) 1993, 44, 297.
6. (c) Crimmins, M. T. in Comprehensive Organic Synthesis, Vol. 5; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; pp 123-150.
7. (d) Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003.
8. For selected recent reports, see: (a) Andrew, D.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5647. (b) Maradyn, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359. (c) Andrew, D.; Hastings, D. I.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870. (d) Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525.
9. For selected recent reports, see: (a) Andrew, D.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5647. (b) Maradyn, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359. (c) Andrew, D.; Hastings, D. I.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870. (d) Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525.
10. For selected recent reports, see: (a) Andrew, D.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5647. (b) Maradyn, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359. (c) Andrew, D.; Hastings, D. I.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870. (d) Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525.
11. For selected recent reports, see: (a) Andrew, D.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5647. (b) Maradyn, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359. (c) Andrew, D.; Hastings, D. I.; Weedon, A. C. J. Am. Chem. Soc. 1994, 116, 10870. (d) Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525.
12. (a) Fraser-Reid, B.; Holder, N. L.; Hicks, D. R.; Walker, D. L. Can. J. Chem. 1977, 55, 3978.
13. (b) Parry, R. J.; Haridas, K.; De Jong, R.; Johnson, C. R. Tetrahedron Lett. 1990, 31, 7549.
14. (c) Buenger, G. S.; Marquez, V. E. Tetrahedron Lett. 1992, 33, 3707.
15. (a) Zimmerman, H. E.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 5245.
16. (b) Zimmerman, H. E.; Little, R. D. J. Am. Chem. Soc. 1974, 96, 4623.
17. (a) Agosta, W. C.; Smith, A. B., III; Kende, A. S.; Eilerman, R. G.; Benham, J. Tetrahedron Lett. 1969, 4517.
18. (b) Agosta, W. C.; Smith, A. B., III. J. Am. Chem. Soc. 1971, 93, 5513.
19. (a) Schreiber, W. L.; Agosta, W. C. J. Am. Chem. Soc. 1971, 93, 3814.
20. (b) Wolff, S. Schreiber, W. L.; Smith, A. B., III; Agosta, W. C. J. Am. Chem. Soc. 1972, 94, 7797.
21. For a review of alternative synthetic approaches to this target, see: Kim, S.; Winkler, J. D. Chem. Soc. Rev. 1997, 26, 387.
22. Katsumura, S.; Isoe, S. Helv. Chim. Acta 1982, 65, 1927.
23. Ketone 1 was prepared by sequential addition of the organocerate derived from (+)-cyclopentenyl bromide i to (+)-norcaranone ii (Paquette, L. A.; O'Neil, S. V.; Guillo, N.; Zeng, Q.; Young, D. G. Synlett 1999, 1857) desilylation, perruthenate oxidation, and ring-closing metathesis. equation presented
24. A third primary photoproduct formed to the extent of 13% in dioxane and 38% in benzene currently remains unidentified.
25. Furxhi, E.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1999, 64, 4064.
26. Another important point is that a methoxy group only slightly accelerates the opening of a cyclopropylcarbinyl radical: Martinez, F. N.; Schlegel, H. B.; Newcomb, M. J. Org. Chem. 1998, 63, 3618.
27. Crich, D.; Huang, X.; Beckwith, A. L. J. J. Org. Chem. 1999, 64, 1762.
28. Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.