Intramolecular photocycloaddition of β-stilbazoles tethered by silyl chains

Tetrahedron Letters

Volumn 47, Issue 45, 2006, Pages 7865-7869

  Maeda, Hajime ^a   Hiranabe, Ryu ichiro ^a   Mizuno, Kazuhiko ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Stilbazole; Dicarboxylic acid; Intramolecular photocycloaddition; Silyl chain; Stilbazolium

Indexed keywords

CATECHOL; DICARBOXYLIC ACID; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; COMPLEX FORMATION; CYCLOADDITION; STEREOCHEMISTRY;

EID: 33749244921     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.021     Document Type: Article

References (49)

1. Williams J.L.R., Webster S.K., and Van Allan J.A. J. Org. Chem. 26 (1961) 4893-4895
2. Quina F.H., and Whitten D.G. J. Am. Chem. Soc. 97 (1975) 1602-1603
3. Quina F.H., and Whitten D.G. J. Am. Chem. Soc. 99 (1977) 877-883
4. Takagi K., Suddaby B.R., Vadas S.L., Backer C.A., and Whitten D.G. J. Am. Chem. Soc. 108 (1986) 7865-7867
5. Banu H.S., Lalitha A., Pitchumani K., and Srinivasan C. Chem. Commun. (1999) 607-608
6. Takagi K., Usami H., Fukaya H., and Sawaki Y. J. Chem. Soc., Chem. Commun. (1989) 1174-1175
7. Usami H., Takagi K., and Sawaki Y. J. Chem. Soc., Perkin Trans. 2 (1990) 1723-1728
8. Usami H., Takagi K., and Sawaki Y. Bull. Chem. Soc. Jpn. 64 (1991) 3395-3401
9. Usami H., Takagi K., and Sawaki Y. J. Chem. Soc., Faraday Trans. 88 (1992) 77-81
10. Lalitha A., Pitchumani K., and Srinivasan C. J. Photochem. Photobiol. A: Chem. 134 (2000) 193-197
11. Li X.-H., Wu L.-Z., Zhang L.-P., and Tung C.-H. Org. Lett. 4 (2002) 1175-1177
12. Takagi K., Shibata S., Oguri S., Sawaki Y., Suzuoki Y., and Segi T. Chem. Lett. (1993) 2103-2106
13. Ohtani O., Kato H., Yui T., and Takagi K. J. Am. Chem. Soc. 125 (2003) 14465-14472
14. Horner M., and Hünig S. J. Am. Chem. Soc. 99 (1977) 6120-6122
15. Horner M., and Hünig S. Liebigs Ann. Chem. (1982) 1183-1210
16. Zhang W.-Q., Zhang X.-H., Zheng Y., Shen G., and Zhuang J.-P. Ganguang Kexue Yu Guang Huaxue 18 (2000) 144-149
17. Pattabiraman M., Natarajan A., Kaliappan R., Mague J.T., and Ramamurthy V. Chem. Commun. (2005) 4542-4544
18. Whitten D.G., Wildes P.D., and DeRosier C.A. J. Am. Chem. Soc. 94 (1972) 7811-7823
19. Bartocci G., Mazzucato U., Masetti F., and Galiazzo G. J. Phys. Chem. 84 (1980) 847-851
20. Takagi K., and Ogata Y. J. Org. Chem. 47 (1982) 1409-1412
21. Takagi K., Aoshima K., Sawaki Y., and Iwamura H. J. Am. Chem. Soc. 107 (1985) 47-52
22. Loader C.E., and Timmons C.J. J. Chem. Soc., C (1966) 1078-1081
23. Arai S., Takeuchi T., Ishikawa M., Takeuchi T., Yamazaki M., and Hida M. J. Chem. Soc., Perkin Trans. 1 (1987) 481-487
24. Lewis F.D., Kalgutkar R.S., and Yang J.-S. J. Am. Chem. Soc. 123 (2001) 3878-3884
25. Maeda H., Nishimura K., Mizuno K., Yamaji M., Oshima J., and Tobita S. J. Org. Chem. 70 (2005) 9693-9701
26. For the related studies on intramolecular photocycloaddition of styrene derivatives tethered by silyl chains:. Nakanishi K., Mizuno K., and Otsuji Y. J. Chem. Soc., Perkin Trans. 1 (1990) 3362-3363
27. Fleming S.A., and Ward S.C. Tetrahedron Lett. 33 (1992) 1013-1016
28. Mizuno K., Nakanishi K., Otsuji Y., Hayamizu T., Maeda H., Adachi T., Ishida A., and Takamuku S. J. Photosci. 10 (2003) 121-126
29. Maeda H., Yagi H., and Mizuno K. Chem. Lett. 33 (2004) 388-389
30. Declercq D., Delbeke P., De Schryver F.C., Van Meervelt L., and Miller R.D. J. Am. Chem. Soc. 115 (1993) 5702-5708
31. Steinmetz M.G. Chem. Rev. 95 (1995) 1527-1588
32. Kyushin S., Ikarugi M., Goto M., Hiratsuka H., and Matsumoto H. Organometallics 15 (1996) 1067-1070
33. Hiratsuka H., Kobayashi S., Minegishi T., Hara M., Okutsu T., and Murakami S. J. Phys. Chem. A 103 (1999) 9174-9183
34. Maeda H., Inoue Y., Ishida H., and Mizuno K. Chem. Lett. (2001) 1224-1225
35. Kyushin S., Takemasa N., Matsumoto H., Horiuchi H., and Hiratsuka H. Chem. Lett. 32 (2003) 1048-1049
36. Karatsu T., Terasawa M., Yagai S., Kitamura A., Nakamura T., Nishimura Y., and Yamazaki I. J. Organomet. Chem. 689 (2004) 1029-1035
37. Karatsu T., Hazuku R., Nishioka D., Yagai S., Kobayashi N., and Kitamura A. J. Photopolym. Sci. Technol. 18 (2005) 65-68
38. Kyushin S., Ishikita Y., Matsumoto H., Horiuchi H., and Hiratsuka H. Chem. Lett. 35 (2006) 64-65
39. Maeda H., Maeda T., Mizuno K., Fujimoto K., Shimizu H., and Inouye M. Chem. Eur. J. 12 (2006) 824-831
40. Heck R.F. Org. React. 27 (1982) 345-390
41. Larhed M., and Hallberg A. In: Negishi E., and de Meijere A. (Eds). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 (2002), John Wiley and Sons, New York, NY 1133-1178
42. Beller M., Zapf A., and Riermeier T.H. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis Vol. 1 (2004), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany 271-305
43. Bräse S., and de Meijere A. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany 217-315
44. 3): δ -3.49, 24.60, 25.48, 123.02, 123.32, 126.41, 127.89, 128.35, 130.62, 132.23, 132.33, 133.08, 134.85, 140.44, 147.89, 148.08.
45. 2 at 298 K.
46. 9b
47. Resorcinol is used as a template for the connection of two molecules of γ-stilbazole and 1,2-bis(4-pyridyl)ethene in the solid state. MacGillivray L.R., Reid J.L., and Ripmeester J.A. J. Am. Chem. Soc. 122 (2000) 7817-7818
48. MacGillivray L.R., Reid J.L., Ripmeester J.A., and Papaefstathiou G.S. Ind. Eng. Chem. Res. 41 (2002) 4494-4497
49. MacGillivray L.R., Papaefstathiou G.S., Friščič T., Varshney D.B., and Hamilton T.D. Top. Curr. Chem. 248 (2004) 201-221