Synthesis of new thiophene-substituted 3,3-diphenyl-3H-naphtho[2,1-b]pyrans by cross-coupling reactions, precursors of photomodulated materials

European Journal of Organic Chemistry

Volumn , Issue 15, 2003, Pages 2799-2812

  Frigoli, Michel ^a   Moustrou, Corinne ^a   Samat, André ^a   Guglielmetti, Robert ^a  

^a AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

Cross coupling; Heterocycles; Photochromism; Synthesis design

Indexed keywords

3,3 DIPHENYL 3H NAPHTHOL[2,1 B]PYRAN; ALCOHOL DERIVATIVE; BORONIC ACID DERIVATIVE; DIPHENYLPROPARGYLIC ALCOHOL; NAPHTHALENE DERIVATIVE; NAPHTHOL DERIVATIVE; PYRAN DERIVATIVE; THIOPHENE DERIVATIVE; THIOPHENIC BORONATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COVALENT BOND; GRIGNARD REACTION; STEREOISOMERISM; SYNTHESIS;

EID: 0043157643     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300033     Document Type: Article

References (67)

1. Molecular Electronics (Ed.: G. J. Ashwell), John Wiley & Sons Inc., New York, 1992.
2. [a] M. Irie, Chem. Rev. 2000, 100, 1685-1716.
3. [b] G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev. 2000, 100, 1741-1753.
4. [c] S. Kawata, Y. Kawata, Chem. Rev. 2000, 100, 1777-1788.
5. [a] S. L. Gilat, S. H. Kawai, J. M. Lehn, J. Chem. Soc., Chem. Commun. 1993, 1439-1442.
6. [b] T. Saika, M. Irie, T. Shimidzu, J. Chem. Soc., Chem. Commun. 1994, 2123-2124.
7. [c] S. L. Gilat, S. H. Kawai, J. M. Lehn, Chem. Eur. J. 1995, 1, 275-284.
8. [d] G. M. Tsivgoulis, J. M. Lehn, Angew. Chem. Int. Ed. Engl. 1995, 34, 1119-1122.
9. [e] S. H. Kawai, S. L. Gilat, R. Ponsinet, J. M. Lehn, Chem. Eur. J. 1995, 1, 285-293.
10. [f] G. M. Tsivgoulis, J. M. Lehn, Chem. Eur. J. 1996, 2, 1399-1406.
11. [g] M. Irie, Bull. Chem. Soc., Jpn. 1998, 71, 985-996.
12. [a] M. Takeshita, M. Irie, Tetrahedron Lett. 1999, 40, 1345-1348.
13. [b] S. H. Kawai, S. L. Gilat, J. M. Lehn, Eur. J. Org. Chem. 1999, 2359-2366.
14. [c] T. Yamagushi, T. Inagawa, H. Nakazumi, S. Irie, M. Irie, Chem. Mater. 2000, 12, 869-871.
15. [d] L. N. Lucas, J. Van Esch, R. M. Kellogg, B. L. Feringa, Chem. Commun. 2001, 759-760.
16. [e] T. Kawai, T. Sasaki, M. Irie, Chem. Commun. 2001, 711-712.
17. Molecular Switches (Ed.: Ben L. Feringa), Wiley-VCH Verlag GmbH, Weinheim, 2001.
18. M. Frigoli, PhD Dissertation, Univ. of Méditerranée, Marseille, 2000.
19. [a] J. L. Pozzo, A. Samat, R. Guglielmetti, V. Lokshin, V. Minkin, Can. J. Chem. 1996, 74, 1649-1659.
20. [b] G. Harié, A. Samat, R. Guglielmetti, D. De Keukeleire, W. Saeyens, I. Van Parys, Tetrahedron Lett. 1997, 38, 3075-3078.
21. [a] G. Horowitz, X. Z. Peng, D. Fichou, F. Garnier, J. Mol. Electron. 1991, 7, 85-89.
22. [b] J. Roncali, Chem. Rev. 1992, 92, 711-738.
23. [c] B. Rasch, W. Vielstich, J. Electroanal. Chem. 1994, 370, 109-117.
24. [d] J. Roncali, Chem. Rev. 1997, 97, 173-205.
25. [e] R. D. McCullough, Adv. Mater. 1998, 10, 93-116.
26. [f] D. Fichou, J. Mater. Chem. 2000, 10, 571-588.
27. Handbook of Oligo- and Polythiophenes (Ed.: D. Fichou), Wiley-VCH, Weinheim, 1999.
28. R. Guglielmetti, in: Photochromism: Molecules and Systems (Ed.: H. Dürr), Elsevier: Amsterdam, 1990, vol. 8, p. 314.
29. B. Van Gemert, in: Organic Photochromic and Thermochromic Compounds (Eds.: J. C. Crano, R. J. Guglielmetti), Plenum Publishing Corporation: New York, 1999, vol. 1, ch. 3, p. 111.
30. G. Harié, A. Samat, R. Guglielmetti, Mol. Cryst. Liq. Cryst. 1997, 297, 263-268.
31. J. L. Pozzo, A. Samat, R. Guglielmetti, R. Dubest, J. Aubard, Helv. Chim. Acta 1997, 80, 725-738.
32. B. Van Gemert, M. Bergomi, D. Knowles, Mol. Cryst. Liq. Cryst. 1994, 246, 67-73.
33. H. G. Heller, to: PPG Industries Inc., WO 92/01959, 1992.
34. C. Moustrou, N. Rebière, A. Samat, R. Guglielmetti, A. E. Yassar, R. Dubest, J. Aubard, Helv. Chim. Acta 1998, 81, 1293-1302.
35. N. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem. 1977, 42, 3772-3774.
36. K. Chamontin, V. Lokshin, G. Garros, A. Samat, R. Guglielmetti, Mol. Cryst. Liq. Cryst. 1997, 298, 7-11.
37. [a] K. Tamao, S. Kodama, I. Nakajima, M. Kumada, Tetrahedron 1982, 38, 3347-3354.
38. [b] A. Carpita, R. Rossi, Gazz. Chim. Ital. 1985, 115, 575-583.
39. [c] A. Carpita, R. Rossi, C. A. Veracini, Tetrahedron 1985, 41, 1919-1929.
40. [d] N. Jayasuriya, J. Kagan, Heterocycles 1986, 24, 2261-2264.
41. [a] R. Rossi, A. Carpita, M. Ciofalo, Gazz. Chim. Ital. 1990, 120, 793-803.
42. [b] R. Rossi, A. Carpita, M. Ciofolo, V. Lippolis, Tetrahedron 1991, 47, 8443-8460.
43. [a] J. M. Mallan, R. L. Bebb, Chem. Rev. 1969, 69, 693-755 and references therein.
44. [b] D. S. Noyce, D. A. Forsyth, J. Org. Chem. 1974, 39, 2828-2831.
45. [c] R. M. Kellogg, A. P. Schaap, H. Wynberg, J. Org. Chem. 1969, 34, 343-346.
46. [d] A. Mac Eachern, C. Soucy, L. C. Leitch, J. T. Arnason, P. Morand, Tetrahedron 1988, 44, 2403-2412.
47. [a] N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513-519.
48. [b] A. Suzuki, Pure Appl. Chem. 1994, 66, 213-222.
49. [c] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
50. [d] A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
51. [a] V. N. Kalinin, Synthesis 1992, 413-432.
52. [b] S. P. Stanforth, Tetrahedron 1998, 54, 263-303.
53. [a] P. J. Stang, M. Hanack, L. R. Subramanian, Synthesis 1982, 85-126.
54. [b] K. Ritter, Synthesis 1993, 735-762.
55. [a] G. T. Crisp, S. Papadopoulos, Aust. J. Chem. 1989, 42, 279-285.
56. [a] J. A. Robl, Synthesis 1991, 56-58.
57. [b] M. S. Newman, V. Sankaran, D. R. Olson, J. Am. Chem. Soc. 1976, 98, 3237-3241.
58. M. Frigoli, C. Moustrou, A. Samat, R. Guglielmetti, Helv. Chim. Acta 2000, 83, 3043-3052.
59. H. Schmidhammer, A. Brossi, J. Org. Chem. 1983, 48, 1469-1471.
60. N. V. Stulin, N. I. Putokhin, Khim. Geterotsikl. Soedin. 1965, 6, 822-824.
61. [a] D. Walker, J. D. Hiebert, Chem. Rev. 1967, 67, 153-195.
62. [b] P. P. Fu, R. G. Harvey, Chem. Rev. 1978, 78, 317-361.
63. [c] M. Tashiro, T. Yamato, K. Kobayashi, T. Arimura, J. Org. Chem. 1987, 52, 3196-3199.
64. R. S. Lott, V. S. Chauhan, C. H. Stammer, J. Chem. Soc., Chem. Commun. 1979, 495-496.
65. M. Frigoli, V. Pimienta, C. Moustrou, A. Samat, R. Guglielmetti, J. Aubard, F. Maurel, J.-C. Micheau, Photobiol. Photochem. Sci. 2003 (in press).
66. S. Coen, C. Moustrou, M. Frigoli, M. Julliard, A. Samat, R. Guglielmetti, J. Photochem. Photobiol. A: Chem. 2001, 139, 1-4.
67. J. W. Akitt, J. Magn. Reson. 1970, 3, 411-414.