Anionic 5-endo-trig Cyclization of Terminally Difluorinated Homoallylic Alkoxides

Journal of Physical Chemistry A

Volumn 103, Issue 34, 1999, Pages 6820-6824

  Yamazaki, Takashi ^a   Hiraoka, Shuichi ^a   Sakamoto, Johei ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000340553     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9907948     Document Type: Article

References (46)

1. (a) Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
2. (b) Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736.
3. For recent representative examples, see: (a) Gao, J.-X.; Rusling, J. F. J. Org. Chem. 1998, 63, 218.
4. (b) Ishibashi, H.; Higuchi, M; Ohba, M.; Ikeda, M. Tetrahedron Lett. 1998, 39, 75.
5. (c) Gimisis, T.; Chatgilialoglu, C. J. Org. Chem. 1996, 61, 1908.
6. (d) Clive, D. L. J.; Cantin, M. J. Chem. Soc., Chem. Commun. 1995, 319.
7. (a) Gao, J.-X.; Rusling, J. F. J. Org. Chem. 1998, 63, 218.
8. (b) Hartung, J.; Stowasser, R.; Vitt, D.; Bringmann, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2820.
9. (c) Beckwith, A. L. J.; Zimmermann, J. J. Org. Chem. 1991, 56, 5791.
10. (d) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.
11. (e) Canadell, E.; Igual, J. J. Chem. Soc., Perkin Trans 2 1985, 1331.
12. (f) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
13. (a) Ichikawa, J.; Wada, Y.; Okauchi, T.; Minami, T. Chem. Commun. 1997, 1537.
14. (b) Craig, D.; Smith, A. M. Tetrahedron Lett. 1992, 33, 695.
15. (c) Chambers, R. D.; Greenhall, M. P. J. Chem. Soc., Chem. Commun. 1990, 1128.
16. (d) Grigg, R.; Kemp, J.; Malone, J. F. Tetrahedron 1988, 44, 5361.
17. (e) Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron Lett. 1985, 26, 4455.
18. For examples where the nitrogen lone pair played an important role, see: (a) Kimura, M.; Harayama, H. Tanaka, S.; Tamara, Y. J. Chem. Soc., Chem. Commun. 1994, 2531.
19. (b) Jung, M. E.; Love, B. E. J. Chem. Soc., Chem. Commun. 1987, 1288. Pent-4-en-1-yl iodide, after transformation into the corresponding iodine difluoride by treatment with xenon difluoride, was reported to cyclize in a 5-endo-trig manner. See: Patrick, T. B.; Zhang, L.-K. Tetrahedron Lett. 1997, 38, 8925.
20. Pent-4-en-1-yl iodide, after transformation into the corresponding iodine difluoride by treatment with xenon difluoride, was reported to cyclize in a 5-endo-trig manner. See: Patrick, T. B.; Zhang, L.-K. Tetrahedron Lett. 1997, 38, 8925.
21. (a) Hiraoka, S.; Yamazaki, T.; Kitazume, T. Heterocycles 1998, 47, 129.
22. (b) Hiraoka, S.; Yamazaki, T.; Kitazume, T. Chem. Commun. 1997, 1497.
23. (c) Hiraoka, S.; Yamazaki, T.; Kitazume, T. Synlett 1997, 669.
24. (d) Yamazaki, T.; Hiraoka, S.; Kitazume, T. Tetrahedron: Asym. 1997, 8, 1157.
25. Hiraoka, S.; Yamazaki, T.; Kitazume, T. Unpublished results. Details will be published as an article elsewhere.
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision C.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
27. Reed, E. A.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
28. (a) Smart, B. E. In Organofluorine Chemistry Principles and Commercial Application: Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Plenum Press: New York, 1994; p 57.
29. (b) Smart, B. E. In Molecular Structure and Energetics: Liebman, J. F., Greenberg, A., Eds.; VCH Publisher: New York, 1986; p 141.
30. For reviews, see: (a) Graczyk, P. P.; Mikolajczyk, M. Top. Stereochem. 1994, 21, 159.
31. (b) Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019.
32. Box, V. G. S. Heterocycles 1990, 31, 1157.
33. In the present text, the stereoelectronic explanation was adopted for the explanation of the anomeric effect, there have been reported several principles. See ref 11 in detail.
34. Lemieux, R. U.; Pavia, A. A.; Martin, J. C.; Watanabe, K. A. Can. J. Chem. 1969, 47, 4427.
35. Cieplak, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 1, 8447.
36. Briggs, A. J.; Glenn, R.; Jones, P. G.; Kirby, A. J.; Ramaswamy, P. J. Am. Chem. Soc. 1984, 106, 6200.
37. Also see: (a) Amps, R. D.; Handy, N. C.; Jones, P. G.; Kirby, A. J.; Parker, J. K.; Percy, J. M.; Su, M.-D. J. Chem. Soc., Perkin Trans. 2 1992, 549.
38. (b) Green, A. J.; Pigdon, T.; White, J. M.; Yamen, J. J. Org. Chem. 1998, 63, 3943.
39. x (X: N, O, S, ...) is called as negative hyperconjugation. Roberts, J. D.; Webb, R. L.; McElhill, E. A. J. Am. Chem. Soc. 1950, 72, 408.
40. For representative articles on the discussion of this topic, also see: (a) Raabe, G.; Gais, H.-J.; Fleischhauer, J. J. Am. Chem. Soc. 1996, 118, 4622.
41. (b) Schneider, W. F.; Nance, B. I.; Wallington, T. J. J. Am. Chem. Soc. 1995, 117, 478.
42. (c) Politzer, P.; Grice, M. E. J. Chem. Res. (S) 1995, 296.
43. (d) Koppel, I. A.; Pihl, V.; Koppel, J.; Anvia, F.; Taft, R. W. J. Am. Chem. Soc. 1994, 116, 8654.
44. (e) Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1993, 115, 614.
45. (f) Rahman, M. M.; Lemal, D. M.; Dailey, W. P. J. Am. Chem. Soc. 1988, 110, 1964.
46. (g) Dixon, D. A.; Fukunaga, T.; Smart, B. E. J. Am. Chem. Soc. 1986, 108, 4027.