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

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1999, Pages 1431-1436

  Butkus, Eugenius ^a   Kubilius, Rytis ^a   Stoncius, Sigitas ^a   Ilinskas, Albinas ^a  

^a VILNIUS UNIVERSITY   (Lithuania)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001013138     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901620a     Document Type: Article

References (52)

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