Tether-enforced reversal of regioselectivity: Head-to-head [4 + 4] photocycloaddition of 2-pyridones

Chemical Communications

Volumn , Issue 19, 1996, Pages 2249-2250

  Sieburth, Scott McN ^a   Siegel, Brian ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345895117     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960002249     Document Type: Article

References (23)

1. Y. Nakamura, T. Kato and Y. Morita, J. Chem. Soc., Perkin Trans. 1, 1982, 1187.
2. (a) S. McN. Sieburth and J.-I. Chen, J. Am. Chem. Soc., 1991, 113, 8163
3. (b) S. McN. Sieburth and P. V. Joshi, J. Org. Chem., 1993, 58, 1661
4. (c) S. McN. Sieburth and K. Ravindran, Tetrahedron Lett., 1994, 35, 3861
5. (d) S. McN. Sieburth, G. Hiel, C.-H. Lin and D. P. Kuan, J. Org. Chem., 1994, 59, 80.
6. E. C. Taylor and W. W. Paudler, Tetrahedron Lett., 1960, 25, 1.
7. Head-to-head isomers have also been reported in photoreactions of 2-pyridones in micelles: Y. Nakamura, T. Kato and Y. Morita, Tetrahedron Lett., 1981, 22, 1025. See also ref. 5.
8. Symmetric N,N′-tethered bis(2-pyridone)s have been reported to undergo photocycloaddition but these differ from other cases discussed as the reactions were run with photosensitizers: Y. Nakamura, J. Zsindely and H. Schmid, Helv. Chim. Acta, 1976, 59, 2841.
9. H. D. H. Showalter and T. H. Haskell, J. Heterocycl. Chem., 1981, 18, 367.
10. M. J. Palmer, J. C. Danilewicz and H. Vuong, Synlett, 1994, 171.
11. E. J. Corey and J. Streith, J. Am. Chem. Soc., 1964, 86, 950.
12. W. J. Begley, G. Lowe, A. K. Cheetham and J. M. Newsam, J. Chem. Soc., Perkin Trans. 1, 1981, 2620.
13. X-ray structures of 2-pyridone photoproducts: M. Laing, Proc. Chem. Soc., London, 1964, 343;
14. J. N. Brown, R. L. R. Towns and L. M. Trefonas, J. Am. Chem. Soc., 1971, 93, 7012;
15. S. McN. Sieburth and C.-H. Lin, Tetrahedron Lett., 1996, 37, 1141 and refs. 2(a-c).
16. E. Vogel, Liebigs Ann. Chem., 1958, 615, 1.
17. Using the MM3 forcefield (ref. 15), as implemented in MACRO-MODEL, ver. 4.0; F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comp. Chem., 1990, 11, 440.
18. S. McN. Sieburth and C.-H. Lin, J. Org. Chem., 1994, 59, 3597.
19. N. C. Yang and J. Libman, J. Am. Chem. Soc., 1972, 94, 9228;
20. P. E. Eaton and U. R. Chakraborty, J. Am. Chem. Soc., 1978, 100, 3634;
21. L. A. Paquette, C. W. Doecke and G. Klein, J. Am. Chem. Soc., 1979, 101, 7599;
22. Y. Tobe, F. Hirata, K. Nishida, H. Fujita, K. Kimura and Y. Odaira, J. Chem. Soc., Chem. Commun., 1981, 786.
23. N. L. Allinger, Y. H. Yuh and J.-H. Lii, J. Am. Chem. Soc., 1989, 111, 8551.