Medium-sized Cyclophanes. Part 40.1 Generation of a Bis(o-quinone methide) from [n.2]Cyclophanes having a Spiro Skeleton and their Trapping Reaction with Nucleophiles and Dienophiles

Abstract

Spiro compounds 2, obtained from the oxidation of dihydroxy[n.2]metacyclophanes 1 with K₃Fe(CN)₆, readily generate a bis(o-quinone methide) 3 with mild heating which is trapped with nucleophiles and dienophiles to give diarylalkanes 4–6 and [4+2] cycloadducts 8, respectively.

References

1. Part 39: T. Yamato, K. Fujita, T. Ando, S. Ide, Y. Nagano and M. Tashiro, J. Chem. Res., 1996, (S) 264; (M) 1434.
2. A. B. Turner, Quart. Rev., 1964, 28, 347.
3. (b) A. Merrijan, B. A. Shoulders and P. D. Gardner, J. Org. Chem., 1963, 28, 2148.
4. A. Bistrzycki and C. Herbst, Chem. Ber., 1903, 36, 2335.
5. L. J. Filar and S. Winstein, Tetrahedron Lett., 1960, 25, 9.
6. D. A. Balon, J. Org. Chem., 1970, 35, 715.
7. D. A. Balon, J. Org. Chem., 1970, 35, 3666.
8. M. Tashiro, T. Yamato, S. Horie and S. Mataka, Chem. Pharm. Bull., 1984, 32, 1641.
9. T. Yamato, J. Matsumoto, K. Tokuhisa, K. Suehiro, S. Horie and M. Tashiro, J. Org. Chem., 1992, 57, 6368.
10. T. Yamato, J. Matsumoto, K. Tokuhisa, K. Suehiro and M. Tashiro, J. Chem. Soc., Chem. Commun., 1992, 865.
11. T. Yamato, K. Fujita, J. Matsumoto, M. Sato, Y. Nagano and M. Tashiro, J. Chem. Res. (S), 1996, 262.
12. (b) M. Tashiro, K. Koya and T. Yamato, J. Am. Chem. Soc., 1982, 104, 3707.
13. A. M. Litwak, F. Grynszpan, O. Aleksiuk, S. Cohen and S. E. Biali, J. Org. Chem., 1993, 58, 393.