Intramolecular ring closure via ether bond in reaction of α,α′-halogeno bicyclo[3.3.1]nonanediones under basic conditions

Abstract

The stereoselectivity of halogenation of bicyclo[3.3.1]nonan-2-one 1 and bicyclo[3.3.1]nonane-2,6-dione 2 with molecular bromine and chlorine was studied. The transformation of α-bromo- and chloro-bicyclo[3.3.1]nonanones 3–5 under Favorskii reaction conditions was studied. The reaction of α,α′-dihalogeno diones in the presence of sodium methoxide, ethoxide, propoxide and potassium cyanide led to the intramolecular ring closure via C–O bond formation giving the highly functionalized chiral 2-oxatricyclo[4.3.1.0^3,8]decane (2-oxaprotoadamantane) structure. Enantiomers of this cage structure were resolved by chiral GLC. The intramolecular ring closure pathway involving the intermediate alkoxybicyclo[3.3.1]nonanolate structure was proposed.

References

1. (a) J. March, Advanced Organic Chemistry, John Wiley and Sons, New York, 1992, p. 1080; (b) T. I. Temnikova and S. N. Semenova, Molecular Rearrangements in Organic Chemistry, Khimiya, Leningrad, 1983, pp. 239–246(in Russian); (c) P. J. Chenier, J. Chem. Educ., 1978, 55, 286; (d) A. A. Akhrem, T. K. Ustynyuk and Y. A. Titov, Russ. Chem. Rev., (Engl. Transl.), 1970, 39, 732.
2. (a) G. Mehta and S. Padma, Tetrahedron, 1991, 47, 7807; (b) L. E. Boyer, J. Brazillo, M. A. Forman and B. Zanoni, J. Org. Chem., 1996, 61, 7611; (c) P. E. Eaton and U. R. Chakraborty, J. Am. Chem. Soc., 1978, 100, 3634.
3. (a) J. Fuchser and A. Zeeck, Liebigs Ann.-Recl., 1997, 87; (b) J. M. Llera and B. Fraser-Reid, J. Org. Chem., 1989, 54, 5544; (c) E. Lee and C. H. Yoon, J. Chem. Soc., Chem. Commun., 1994, 479; (d) D. Bai, R. Xu, G. Chu and X. Zhu, J. Org. Chem., 1996, 61, 4600.
4. (a) V. Moliner, R. Castillo, V. S. Safont, M. Oliva, S. Bohn, I. Tunon and J. Andres, J. Am. Chem. Soc., 1997, 119, 1941 and references cited therein; (b) R. Castillo, V. Moliner and V. S. Safont, J. Mol. Struct. (THEOCHEM), 1998, 426, 299; (c) T. R. Barbee, H. Guy, M. J. Heeg and K. F. Albizati, J. Org. Chem., 1991, 56, 6773.
5. (a) E. Butkus, U. Berg, A. Stončius and A. Rimkus, J. Chem. Soc., Perkin Trans. 2, 1998, 2547; (b) U. Berg, E. Butkus, T. Frejd and S. Bromander, Tetrahedron, 1997, 53, 5339; (c) E. Butkus, U. Berg, A. Stoncius and A. Zilinskas, Mendeleev Commun., 1995, 96; (d) U. Berg and E. Butkus, J. Chem. Res. (S, 1993, 116.
6. S. E. Denmark and W. Lee, J. Org. Chem., 1994, 59, 707.
7. (a) F. G. Riddell, Magn. Reson. Chem., 1992, 30, 1070; (b) N. S. ZeWrov and V. A. Palyulin, Top. Stereochem., 1991, 20, 171.
8. H. Nagaoka, K. Shibuya and Y. Yamada, Tetrahedron, 1994, 50, 661.
9. (a) H. Quast, C. Becker, M. Witzell, E.-M. Peters and H. G. von Schnering, Liebigs Ann., 1996, 985; (b) H. Quast, Janssen Chim. Acta, 1986, 4, 24; (c) R. J. K. Taylor, S. M. Turner and D. C. Horwell, J. Chem. Soc., Perkin Trans. 1, 1990, 2145; (d) T. Momose, O. Muraoka and K. Masuda, Chem. Pharm. Bull., 1989, 37, 1645; (e) M. Nakazaki, Top. Stereochem., 1982, 11, 15; (f) C. E. Marjo, M. L. Scudder, D. C. Craig and R. Bishop, J. Chem. Soc., Perkin Trans. 2, 1997, 2099.
10. (a) T. Itooka, K. Matobe, T. Yamazaki, O. Muraoka and T. Momose, Chem. Pharm. Bull., 1986, 34, 2391; (b) F. Kurzer and J. N. Patel, Monatsh. Chem., 1987, 118, 1363.
11. E. P. Butkus, A. J. Zilinskas, P. P. Kadziauskas and R. R. Kubilius, Russ. Chem. Bull., 1997, 46, 328.
12. C. S. Burgey, R. Vollerthun and B. Fraser-Reid, J. Org. Chem., 1996, 61, 1609.
13. R. A. Appleton, C. Egan, J. M. Evans, S. H. Graham and J. R. Dixon, J. Chem. Soc. C, 1968, 1110.
14. T. A. Klimova, M. M. Krayushkin, V. V. Sevost'yanova, S. S. Novikov and N. F. Karpenko, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1975, 24, 1565.
15. H. Quast, C. Becker, E. Geissler, K. Knoll, E.-M. Peters, K. Peters and H. G. von Schnering, Liebigs Ann. Chem., 1994, 109.
16. E. J. Corey, J. Am. Chem. Soc., 1953, 75, 2301.
17. (a) P. J. Chenier and J. C. Kao, J. Org. Chem., 1976, 41, 3730; (b) A. A. O. Sarhan, Monatsh. Chem., 1997, 128, 79.
18. Chemical Abstracts name for this structure is octahydro-2,5-methano-1-benzofuran. A trivial name isotwistane was also used for this structure.¹⁹.
19. C. Ganter, Top. Curr. Chem., 1976, 23, 15.
20. E. Pretsch, T. Clerc, J. Seibl and W. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer, Berlin, 1989. Chemical shifts were also simulated using the ACD/Lab Web free service version 2. 6 at http://www/acdlabs.com/.
21. H. Fisch, S. Smallcombe and J. C. Gramain, J. Org. Chem., 1970, 35, 1886.
22. (a) A. V. Kessenikh, E. N. Aredova, V. V. Sevost'yanova and M. M. Krayushkin, Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 2386; (b) A. Heumann and H. Kolshorn, Tetrahedron, 1975, 31, 1571.
23. We thank one of the Referees for bringing our attention to this point.
24. (a) T.-J. Lu, S.-W. Liu and S.-H. Wang, J. Org. Chem., 1993, 58, 7945; (b) S. Karimi, K. G. Grohmann and L. Todaro, J. Org. Chem., 1995, 60, 554.
25. T. Hasegawa, T. Nigo, Y. Kuwatani and I. Ueda, Bull. Chem. Soc. Jpn., 1993, 66, 2676.
26. SPARTAN Plus, version 1, Wavefunction, Inc., 1840 Von Kazman Avenue, Suite 370, Irvine, CA 92612.
27. M. Hartman, Z. Chem., 1966, 6, 182.
28. (a) H. Meerwein and W. Schürmann, Justus Liebig's Ann. Chem., 1913, 398, 196; (b) D. A. Lightner, T. C. Chang, D. T. HefelWnger, D. E. Jackman, W. M. D. Wijekoon and J. W. Givens, J. Am. Chem. Soc., 1985, 107, 7499.