Ring-enlargement reaction of alkylidenecarbenes bearing a cyclic ether or acetal group. Formation of medium-sized cyclic enol ethers or dienol ethers via bicycloalkenyloxonium ylides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 21, 1998, Pages 3623-3628

  Mori, Takashi ^a   Taniguchi, Masahiko ^a   Suzuki, Fumito ^a   Doi, Hisashi ^a   Oku, Akira ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750247335     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803078b     Document Type: Article

References (46)

1. K. Kondo, I. Tabushi, R. Noyori and S. Fujita, Carbenes, Ylides, Nitrenes and Benzynes, ed. T. Goto, Hirokawa, Tokyo, 1976.
2. The lifetimes of ethereal oxonium ylides are too short for them to be identified by spectroscopic methods. Therefore, their intermediacy has been demonstrated indirectly: (a) I. Naito, A. Oku, N. Ohtani, H. Tanimoto and H. Fujiwara, J. Chem. Soc., Perkin Trans. 2, 1996, 725;
3. (b) T. Sueda, T. Nagaoka, S. Goto and M. Ochiai, J. Am. Chem. Soc., 1996, 118, 10141.
4. For examples of intermolecular oxonium ylide formation, see: (a) H. Nozaki, H. Takaya and R. Noyori, Tetrahedron Lett., 1966, 7, 2563;
5. (b) K. Friedrich, U. Jansen and W. Kirmse, Tetrahedron Lett., 1985, 26, 193;
6. (c) H. Iwamura and Y. Imahasi, Tetrahedron Lett., 1975, 1401;
7. (d) G. A. Olah, H. Doggweiler and J. D. Felberg, J. Org. Chem., 1984, 49, 2116;
8. (e) M. S. Baird, A. G. W. Baxter, A. Hoorter and I. Jefferson, J. Chem. Soc., Perkin Trans. 1, 1991, 2575;
9. (f) F. G. West, T. H. Eberlein and R. W. Tester, J. Org. Chem., 1992, 57, 3479;
10. (g) M. P. Doyle, J. H. Griffin, M. S. Chinn and D van Leusen, J. Org. Chem., 1984, 49, 1917;
11. (h) M. C. Pirrung, W. L. Brown, S. Rege and P. Laughton, J. Am. Chem. Soc., 1991, 113, 8561;
12. (i) J. C. Gilbert and U. Weerasooriya, Tetrahedron Lett., 1980, 21, 2041.
13. For examples of intramolecular oxonium ylide formation, see: (a) J. S. Clark, A. G. Dossetter and W. G. Whittingham, Tetrahedron Lett., 1996, 37, 5603;
14. (b) J. S. Clark and G. A. Whitlock, Tetrahedron Lett., 1994, 35, 6381;
15. (c) M. C. Pirrung and J. A. Werner, J. Am. Chem. Soc., 1986, 108, 6060.
16. A. Oku, S. Ohwaki and K. Kimura, Acta Chem. Scand., 1993, 47, 391.
17. (a) A. Padwa and S. F. Hornbuckle, Chem. Rev., 1991, 91, 263;
18. (b) A. Padwa and K. E. Krumpe, Tetrahedron, 1992, 48, 5385.
19. (a) C. J. Moody and R. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 1989, 721;
20. (b) M. J. Davies, C. J. Heslin and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473;
21. (c) M. J. Davies, C. J. Moody and R. J. Taylor, Synlett, 1990, 93.
22. (a) A. Oku, S. Ohki, T. Yoshida and K. Kimura, Chem. Commun., 1996, 1077;
23. (b) A. Oku, N. Murai and J. Baird, J. Org. Chem., 1997, 62, 2123;
24. (c) T. Kamada, Ge-Quin, M. Abe and A. Oku, J. Chem. Soc., Perkin Trans. 1, 1996, 413.
25. Other diazomethylation reagents such as diazomethyl(trimethyl)-silane in combination with n-BuLi were not successful for this purpose.
26. For the standard procedure of diazomethylation, see: (a) D. Seyferth, R. S. Marmor and P. Hilbert, J. Org. Chem., 1971, 36, 1379;
27. (b) E. W. Colvin and B. Hamill, J. Chem. Soc., Perkin Trans. 1, 1977, 869;
28. (c) J. C. Gilbert and U. Weerasooriya, J. Org. Chem., 1979, 44, 4997;
29. (d) J. C. Gilbert, D. H. Giamalva and U. Weerasooriya, J. Org. Chem., 1983, 48, 5251;
30. (e) J. C. Gilbert and B. K. Blackburn, J. Org. Chem., 1986, 51, 3656 and 4087;
31. (f) S. Ohira, K. Okai and T. Moritani, J. Chem. Soc., Chem. Commun., 1992, 721.
32. MeOH was used as a protic nucleopnile to trap the ylide.
33. 5O, 3%) was obtained, which was presumed to be formed from oxonium ylide of 3a with diethyl ether.
34. 8a was treated with DAMP and t-BuOK in diethyl ether under similar reaction conditions, an isomeric mix of ethereal products 24 (isomer ratio = 2.5) was isolated in 78% yield. For spectral data of 24, see the Experimental section. (Chemical Equation Presented)
35. Isolated diene 16a was treated independently over silica gel and was shown to be intact under the same conditions.
36. Two configurations, cis,cis and cis,trans, have been reported for cycloocta-1,3-diene and cyclodeca-1,3-diene, respectively. (a) W. J. Leigh, K. Zheng, N. Nguyen, N. H. Werstiuk and J. Ma, J. Am. Chem. Soc., 1991, 113, 4993;
37. (b) A. T. Blomquist and A. Goldstein, J. Am. Chem. Soc., 1954, 77, 998.
38. S. Ohira, I. Noda, T. Mizobata and M. Yamato, Tetrahedron Lett., 1995, 36, 3375. They presumed that 2-cyanopropionate could be formed from pyruvate via the corresponding azines of diazoalkene [eqn. (9)]. (Chemical Equation Presented)
39. T. Shono, Y. Matsumura, O. Onomura and Y. Yamada, Synthesis, 1987, 1099.
40. R. Bihovsky, M. U. Kumar, S. Ding and A. Goyal, J. Org. Chem., 1989, 54, 4291.
41. A. P. Krapcho and A. J. Lovey, Tetrahedron Lett., 1973, 957.
42. V. Berens and H. D. Scharf, J. Org. Chem., 1995, 60, 5127.
43. C. S. Marvel and F. D. Hager, Org. Synth., 1932, Coll. Vol. 9, 248.
44. M. Bertrand, G. Leandri and A. Meou, Tetrahedron, 1981, 37, 1703.
45. J. A. Hyatt, J. Org. Chem., 1983, 48, 129.
46. J. C. Gilbert and B. K. Blackburn, J. Org. Chem., 1986, 51, 656.