Base-induced photorearrangements from 3-styrylfurans to 2-methylnaphthalenes

Tetrahedron Letters

Volumn 52, Issue 52, 2011, Pages 7199-7201

  Ho, Jinn Hsuan ^a   Lee, Tunng Hsien ^a   Lo, Chia Kai ^a   Chuang, Chao Li ^a  

^a NATIONAL TAIWAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

Author keywords

2 Methylnaphthalenes; 3 Styrylfurans; Base induced photorearrangement; Photocyclization

Indexed keywords

2 METHYLNAPHTHALENE; 3 (4 SUBSTITUTED STYRYL)FURAN; 7 SUBSTITUTED 2 METHYLNAPHTHALENE; BASE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; IRRADIATION; ISOMERIZATION; PHOTOCHEMISTRY;

EID: 82255179001     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.141     Document Type: Article

References (51)

1. K.A. Muszkat Top. Curr. Chem. 88 1980 89
2. K.B. Jørgensen Molecules 15 2010 4334
3. F.B. Mallory, and C.W. Mallory Org. React. 30 1980 1
4. M.V. Sargent, and C.J. Timmons J. Chem. Soc. 1964 5544
5. W.M. Moore, D.D. Morgan, and F.R. Stermitz J. Am. Chem. Soc. 85 1963 829
6. F.B. Mallory, M.J. Rudolph, and S.M. Oh J. Org. Chem. 54 1989 4619
7. R.G. Giles, and M.V. Sargent J. Chem. Soc., Chem. Commun. 1974 215
8. A.G. Neo, C. López, V. Romero, B. Antelo, J. Delamano, A. Pérez, D. Fernández, J.F. Almeica, L. Castedo, and G. Tojo J. Org. Chem. 75 2010 6764
9. A. Buquet, A. Couture, and A. Lablache-Combier J. Org. Chem. 44 1979 2300
10. J.B.M. Somers, A. Couture, A. Lablache-Combier, and W.H. Laarhoven J. Am. Chem. Soc. 107 1985 1387
11. T.-I. Ho, J.-H. Ho, and J.-Y. Wu J. Am. Chem. Soc. 122 2000 8575
12. J.-H. Ho, T.-I. Ho, and R.S.H. Lu Org. Lett. 3 2001 409
13. I. Škorić, I. Kiks, M. Kovacsb, M. Šindler-Kulyk, and O. Horváth J. Photochem. Photobiol. A 211 2010 152
14. I. Kiks, I. Škorić, Ž. Marinić, and M. Šindler-Kulyk Tetrahedron 66 2010 9405
15. I. Škorić, I. Flegar, Ž. Marinić, and M. Šindler-Kulyk Tetrahedron 62 2006 7396
16. S. Samori, M. Hara, T.-I. Ho, S. Tojo, K. Kawai, M. Endo, M. Fujitsuka, and T. Majima J. Org. Chem. 70 2005 2708
17. J.-H. Ho, and T.-I. Ho Tetrahedron Lett. 44 2003 4669
18. T.-I. Ho, J.-Y. Wu, and S.-L. Wang Angew. Chem., Int. Ed. 38 1999 2558
19. J.-Y. Wu, J.-H. Ho, S.-M. Shih, T.-L. Hsieh, and T.-I. Ho Org. Lett. 1 1999 1039
20. B. Antelo, L. Castedo, J. Delamano, A. Gmez, C. Lpez, and G. Tojo J. Org. Chem. 61 1996 1188
21. G. Karminski-Zamola, L. Fišer-Jakic, and K. Jakopcic Tetrahedron 38 1982 1329
22. K. Oda, H. Tsujita, M. Sakai, and M. Machida Heterocycles 42 1996 121
23. M. Šindler-Kulyk, I. Škorić, S. Tomšić , Ž. Marinić, and D. Mrvoš-Sermek Heterocycles 51 1999 1355
24. W.S. Wadsworth Jr. Synthetic Applications of Phosphoryl-Stabilized Anions W.G. Dauben, Organic Reactions Vol. 25 1977 Wiley New York 73
25. Some cases of methanol addition in methoxystilbenes: J. Woning, A. Oudenampsen, and W.H. Laarhoven J. Chem. Soc., Perkin Trans. 2 1989 2147
26. J.C. Roberts, and J.A. Pincock J. Org. Chem. 69 2004 4279
27. J.C. Roberts, and J.A. Pincock J. Org. Chem. 71 2006 7480
28. F.D. Lewis, T.-I. Ho, and J.T. Simpson J. Org. Chem. 46 1981 1077
29. F.D. Lewis, T.-I. Ho, and J.T. Simpson J. Am. Chem. Soc. 104 1982 1924
30. Y. Yoshimi, S. Hayashi, K. Nishikawa, Y. Haga, K. Maeda, T. Morita, T. Itou, Y. Okada, N. Ichinose, and M. Hatanaka Molecules 15 2010 2623
31. D.V. Bent, and D. Schulte-Frohlinde J. Phys. Chem. 78 1974 446
32. K. Schaffner, H. Wolf, S.M. Rosenfeld, R.G. Lawler, and H.R. Ward J. Am. Chem. Soc. 94 1972 6553
33. W. Adam, and R.S. Oestrich J. Am. Chem. Soc. 114 1992 6031
34. M. Auzias, D. Häussinger, M. Neuburger, and H.A. Wegner Org. Lett. 13 2011 474
35. S. Buscemi, G. Cusmano, and M. Gruttadauria J. Heterocycl. Chem. 27 1990 861
36. P.J. Campos, E. Añn, M.C. Malo, and M.A. Rodríguez Tetrahedron 55 1999 14079
37. M. Sarker, T. Shahrin, and M.G. Steinmetz Org. Lett. 13 2011 872
38. J. Jia, M. Sarker, M.G. Steinmetz, R. Shukla, and R. Rathore J. Org. Chem. 73 2008 8867
39. J. Jia, M.G. Steinmetz, R. Shukla, and R. Rathore Tetrahedron Lett. 49 2008 4621
40. a for the enol of phenylacetaldehyde, PhCCHOH is 9.45. Y. Chiang, and A.J. Kresge J. Am. Chem. Soc. 111 1989 2355
41. M. Tofi, T. Georgiou, T. Montagnon, and G. Vassilikogiannakis Org. Lett. 7 2005 3347
42. W.A.L. van Otterlo, and C.B. de Koning Chem. Rev. 109 2009 3743
43. D. Mal, and P. Pahari Chem. Rev. 107 2007 1892
44. C.B. de Koning, A.L. Rousseaub, and W.A.L. van Otterloa Tetrahedron 59 2003 7
45. C. Dallaire, I. Kolber, and M. Gingras Org. Synth. 78 2002 42
46. K.M. Yadav, P.K. Mohanta, H. Ila, and H. Junjappa Tetrahedron 52 1996 14049
47. D.D. Mazza, and M.G. Reinecke J. Org. Chem. 53 1988 5799 5806
48. W. Baker, J.F.W. McOmic, and W.K. Warburton J. Chem. Soc. 1952 2991
49. H. Koshio, T. Ishihara, H. Yamada, F. Hirayama, Y. Matsumoto, and I. Yanagisawa Chem. Pharm. Bull. 53 2005 448
50. L. Bianchi, C. Dell'Erba, M. Maccagno, G. Petrillo, E. Rizzato, F. Sancassan, E. Severi, and C. Tavani J. Org. Chem. 70 2005 8734
51. T.R. Kelly, R.A. Silva, H. De Silva, S. Jasmin, and Y. Zhao J. Am. Chem. Soc. 122 2000 6935