A novel intramolecular photocyclization of methyl 2-(2,3-dimethylbut-2-enyloxymethyl)naphthalene-1-carboxylate via 1,9-hydrogen abstraction

Abstract

Irradiation of a benzene solution containing methyl 2-(2,3-dimethylbut-2-enyloxymethyl)naphthalene-1-carboxylate 1 gave an eight-membered keto ether 2 as the main product via a novel 1,9-hydrogen abstraction of the ester carbonyl group.

References

1. For a review, see: P. J. Wagner, Acc. Chem. Res., 1971, 4, 168; 1983, 16, 461; 1989, 22, 83.
2. For a review, see: R. Breslow, Acc. Chem. Res., 1980, 13, 170.
3. R. M. Duhaime, D. A. Lombardo, I. A. Skinner and A. C. Weedon, J. Org. Chem., 1985, 50, 873; T. Gomibuchi, K. Fujiwara, T. Nehira and M. Hirama, Tetrahedron Lett., 1993, 34, 5753.
4. K. Fukui and Y. Odaira, Tetrahedron Lett., 1969, 10, 2887.
5. J. J. McCullough, W. K. MacInnis, C. J. L. Lock and R. Faggiani, J. Am. Chem. Soc., 1982, 104, 4644.
6. K. Mizuno, S. Konishi, T. Takata and H. Inoue, Tetrahedron Lett., 1996, 37, 7775.
7. Methyl naphthalene-1-carboxylate (E_T= 256 kJ mol^–1); S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry, Marcel Dekker, New York, 1993, p. 17, 76 and 77.
8. Photocleavage reaction via photoinduced electron transfer: F. D. Saeva, in Photoinduced Electron Transfer I, ed. J. Mattay, Springer-Verlag, Berlin, 1990, pp. 59–92.