On the reaction of (vinylimino)phosphoranes and related compounds.1 Novel synthesis and properties of [n](2,4)pyridinophanes and [n](2,4)quinolinophanes (n = 9-7)

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 21, 1999, Pages 3199-3205

  Miyabara, Hideo ^a   Takayasu, Tohru ^a   Nitta, Makoto ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006312864     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904790e     Document Type: Article

References (46)

1. A preliminary account of this paper has appeared: H. Miyabara, T. Takayasu and M. Nitta, Hcterocycles, 1999,51, 983.
2. The older literature has been reviewed: P. M. Keehn and B. M. Roscnfeld, Cycloplumes, Academic Press, New York, 1983.
3. Review on small cyclophanes: V. V. Kane, W. H. de Wolf and F. Bickelhaupt, Tetrahedron, 1994,50,4575.
4. Y.Tobe, Top. Curr. Cl,e, 1994, 172, 1.
5. G. J. Bodwell, Angeu: Chein., Int. Ed. Engl., 1996,35, 2085.
6. G. B. M. Kostermans, M. Bobeldijk, W H. de Wolf and F. Bickelhaupt, J. Am. Client. Soc., 1987, 109, 2471;
7. T. Tsuji and S. Nishida, J. Am. Client. Soc., 1988, 110, 2157;
8. T. Tsuji, S. Nishida, M. Okuyama and E. Osawa, J. Ant. Client. Soc., 1995, 117, 9804;
9. M. Okuyama and T. Tsuji, Angcn: Chem., Int. Ed. Engl., 1997, 36, 1085.
10. J. E. Rice, T. J. Lee, R. B. Remington, W. D. Allen, D. A. Clabo, Jr. and H. F. Schaefer III, J. Am. Chem. Soc., 1987, 109, 2902;
11. B. Ma, H. M. Sulzbach, R. B. Remincton and H. F. Schaefer III, J. Am. Chem. Soc., 1995, 117,8392.
12. T. Kobayashi and M. Nitta, Bull. Chem. Soc. Jpn., 1985, 58, 3099.
13. H. Gerlach and E. Huber, lieh: Cliim. Ada, 1968, 51, 3099;
14. N. Kanomata and T. Nakata, Angew. Chem., Int. Eel. Engl., 1997, 36, 1207.
15. M. J. van Eis, F. J. J. de Kanter, W. H. de Wolf and F. Bickelhaupt, J. Am. Chem. Soc., 1998, 120, 3371.
16. G. B. M. Kostermans, P. van Dansik, W. H. de Wolf and F. Bickelhaupt, J. Am. Chem. Soc., 1987, 109, 7887.
17. D. Dhanak and C. B. Reese, J Chem. Soc., Perkin Trans, l, 1987, 2829.
18. A. Marchcsini, S. Bradamantc, R. Fusco and G. Pagani, Tetrahedron Lett., 1971, 671; T. Oikawa, N. Kanomata and M. Tada, J. Org. Chem., 1993,58,2046.
19. K. Biemann, G. Büchi and B. H. Walker, J. Am. Chem. Soc., 1957,79, 5558;
20. S. Fujita and H. Nozaki, Bull. Chem. Soc. Jpn., 1971,44,2827;
21. K. Tamao, S. Kodama, T. Nakatsuka, Y. Kiso and M. Kumada, J. Am. Chem. Soc., 1975,97,4405.
22. A. Balaban, Tetrahedron Lett., 1968, 4643; 1978, 5055.
23. W. E. Parham, R. W. Davenport and J. B. Biasotti, Tetrahedron Lett., 1969, 557;
24. W. E. Parham, K. B. Sloan and J. B. Biasotti, Tetrahedron, 1971, 27, 5767;
25. W. E. Parham, D. C. Egbcrg and S. S. Salgar, J. Org. Chem., 1972,37,3248.
26. W. E. Parham, R. Davenport and J. B. Biasotti, J. Org. Chem., 1970, 35, 3775.
27. N. Kanomata and M. Nitta, Tetrahedron Lett., 1998, 29, 5957; J. Chem. Soc., Perkin Trims. I, 1990, 1119.
28. M. Nitta, T. Akie and Y. lino, J. Org. Chem., 1994,59, 1309.
29. For recent reviews: (a) Y. G. Gololobov and L. F. Kasukhin, Tetrahedron, 1992, 48, 1353;
30. (b) S. Eguchi, Y. Matsushita and K. Yamashita, Orç. Prep. I'roced. Int., 1992, 24, 209;
31. M. Nitta, Rev. Heteroalom Cliaii, 1993, 9, 87;
32. P. Molina and M. J. Vilaplana, Synthesis, 1994, 1197;
33. (e) H. WamholT, G. Richard! and S. Stolben, Adv. Heterocycl. Clicm., 1995, 64, 159.
34. J. L. Ripoll, H. Lebrun and A. Thuillier, Tetrahedron, 1980, 36, 2497.
35. W. Dammcrtz and E. Rcimann, Arcli. Pliarin. (Weinhciin, Ger.), 1977, 172;
36. M. J. Lacey, Ausi. J. Client., 1970, 23, 841;
37. P. G. Baraldi, D. Simoni and S. Manfredini, Synthesis, 1983, 902.
38. T. Mulamba, R. E. B. Garré, D. Séraphin, E. Noé, C. C. Fagnère, J. Hérin, J. Laronzc, J. Sapi, R. Barrel, J.-Y. Laronze and J. Levy, Hetcrocycles, 1995,41, 29, and references cited therein.
39. See Dynamic Nuclear Resonance Spectroscopy, éd. L. M. Jackmail_ and F. A. Cotton, Academic Press, New York, 1975.
40. N. L. Allinger, T. J. Walter and M. G. Newton, J. Am. Client. Soc., 1974, 96, 4588;
41. S. Hirano, H. Hara, T. Hiyama, S. Fujita and H. Nozaki, Tetrahedron, 1975, 31, 2219.
42. N. L. Allincer, J. T. Spraauc and T. Liljefors, J. Am. Chem. Soc., 1974,96,5100.
43. J. I. Secman, Pure Appl. Chan., 1987, 59, 1661, and references cited therein.
44. AMI calculations: MOPAC Ver. 6.00, J. J. P. Stewart, QCPA Bull., 19S9, 9, 10; Revised as Ver. 6.12 by D. Arthansopoulos, QCPM, 1994, 137.
45. J. Wohllebe and E. W. Garbisch, Jr., Org. Synlli., 1988, Coll. Vol. 6, 368;
46. E. W. Garbisch, Jr. and J. Wohllebe, J. Org. Clicm., 1968, 33, 2157.