A Novel Strategy for Cyclobutane Formation. Fine Tuning of Cyclobutanation vs Cyclopropanation

Journal of Organic Chemistry

Volumn 63, Issue 10, 1998, Pages 3371-3375

  Yamazaki, Shoko ^a   Kumagai, Hitoshi ^a   Yamabe, Shinichi ^a   Yamamoto, Kagetoshi ^b  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001665319     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972310e     Document Type: Article

References (42)

1. For reviews, see: (a) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 579-627. (b) Knölker, H.-J. J. Prakt. Chem. 1997, 339, 304.
2. For reviews, see: (a) Panek, J. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 579-627. (b) Knölker, H.-J. J. Prakt. Chem. 1997, 339, 304.
3. (a) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144.
4. (b) Knölker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612.
5. Monti, H.; Audran, G.; Léandri, G.; Monti, J.-P. Tetrahedron Lett. 1994, 35, 3073.
6. Monti, H.; Audran, G.; Monti, J.-P.; Léandri, G. Synlett 1994, 403.
7. (a) Akiyama, T.; Kirino, M. Chem. Lett. 1995, 723.
8. (b) Akiyama, T.; Vamanaka, M. Synlett 1996, 1095.
9. (a) Yamazaki, S.; Tanaka, M.; Yamaguchi, A.; Yamabe, S. J. Am. Chem. Soc. 1994, 116, 2356.
10. (b) Yamazaki, S.; Katoh, S.; Yamabe, S. J. Org. Chem. 1992, 57, 4.
11. Yamazaki, S.; Tanaka, M.; Inoue, T.; Morimoto, N.; Kumagai, H. J. Org. Chem. 1995, 60, 6546.
12. Yamazaki, S.; Tanaka, M.; Yamabe, S. J. Org. Chem. 1996, 61, 4046.
13. (e) Yamazaki, S.; Kumagai, H.; Takada, T.; Yamabe, S.; Yamamoto, K. J. Org. Chem. 1997, 62, 2968.
14. Hall, H. K., Jr.; Sentman, R. C. J. Org. Chem. 1982, 47, 4572.
15. (a) Yamazaki, S.; Fujitsuka, H.; Yamabe, S. J. Org. Chem. 1992, 57, 5610.
16. (b) Yamazaki, S.; Fujitsuka, H.; Takara, F.; Inoue, T. J. Chem. Soc., Perkin Trans. 1 1994, 695.
17. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
18. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
19. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
20. A semiempirical method (PM3) was also attempted; however, the geometric results were not reasonable.
21. 4-containing systems, the 6-311G basis set is not available in Gaussian 94.
22. For theoretical studies of the β-silicon effect, see: (a) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. (b) Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
23. For theoretical studies of the β-silicon effect, see: (a) Wierschke, S. G.; Chandrasekhar, J.; Jorgensen, W. L. J. Am. Chem. Soc. 1985, 107, 1496. (b) Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
24. For solvolysis studies of the β-silicon effect, see: (c) Lambert, J. B.; Wang, G.-t.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. (d) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. (e) Lambert, J. B.; Emblidge, R. W.; Malany, S. J. Am. Chem. Soc. 1993, 115, 1317.
25. For solvolysis studies of the β-silicon effect, see: (c) Lambert, J. B.; Wang, G.-t.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. (d) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. (e) Lambert, J. B.; Emblidge, R. W.; Malany, S. J. Am. Chem. Soc. 1993, 115, 1317.
26. For solvolysis studies of the β-silicon effect, see: (c) Lambert, J. B.; Wang, G.-t.; Finzel, R. B.; Teramura, D. H. J. Am. Chem. Soc. 1987, 109, 7838. (d) Lambert, J. B.; Chelius, E. C. J. Am. Chem. Soc. 1990, 112, 8120. (e) Lambert, J. B.; Emblidge, R. W.; Malany, S. J. Am. Chem. Soc. 1993, 115, 1317.
27. See also, (f) Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211.
28. 2 at room temperature for 5 h resulted in recovery of 7a, and no desilylated 8 was produced. The control experiment showed that the trimethylsilyl group was not lost from 7a to form 8 under the reaction conditions.
29. 13C NMR did not show significant differences in chemical shifts between free 2 and Lewis acid-2 complexes. This result suggests that the equilibrium constants for complexation of Lewis acids and 2 are small.
30. Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricci, A. Synlett 1997, 681.
31. Formation of 8 can possibly be caused by protons generated from trace amounts of water in situ. Desilylation of D and subsequent protonation would give intermediate F, which leads to cyclobutane 8. Chemical equations presented.
32. 4 in 2 without Lewis acid. Srisiri, W.; Padias, B. A.; Hall, H. K., Jr. J. Org. Chem. 1994, 59, 5424.
33. Hall, H. K., Jr.; Reineke, K. E.; Ried, J. H.; Sentman, R. C.; Miller, D. J. Polym. Sci., Polym. Chem. Ed. 1982, 20, 361.
34. (a) Huisgen, R. Acc. Chem. Res. 1977, 10, 117 and 199.
35. (b) Huisgen, R.; Brückner, R. Tetrahedron Lett. 1990, 31, 2553.
36. Brückner, R.; Huisgen, R. Tetrahedron Lett. 1990, 31, 2557 and 2561.
37. For reviews, see: (a) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 797. (b) Fujiwara, T.; Takeda, T. J. Synth. Org. Chem. 1994, 52, 498.
38. For reviews, see: (a) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 797. (b) Fujiwara, T.; Takeda, T. J. Synth. Org. Chem. 1994, 52, 498.
39. For the preparation of cyclobutenes, see: (c) Negishi, E.; Liu, F.; Choueiry, D.; Mohamud, M. M. J. Org. Chem. 1996, 61, 8325 and references therein.
40. (a) Burgess, K.; Li, S.; Rebenspies, J. Tetrahedron Lett. 1997, 38, 1681.
41. (b) Gourdel-Martin, M.-E.; Huet, F. J. Org. Chem. 1997, 62, 2166.
42. Hanrahan, J. R.; Taylor, P. C.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1997, 493.