Utilization of industrially available 2,3-dichloro-1,3-butadiene for direct synthesis of 2,3-diaryl-1,3-butadienes

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 3, 2006, Pages 498-500

  Yamamoto, Takakazu ^a   Yasuda, Takuma ^a   Kobayashi, Kazuaki ^a   Yamaguchi, Isao ^a   Koizumi, Take Aki ^a   Ishii, Daisuke ^a   Nakagawa, Masaru ^a   Mashiko, Yoshihiro ^b   Shimizu, Norihiro ^c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Denki Kagaku Kogyo K K   (Japan)

^c DENKA COMPANY LIMITED   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS; DODECYLOXYPHENYL;

CATALYSIS; INDUSTRIAL APPLICATIONS; NICKEL; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BUTADIENE;

1,3 BUTADIENE DERIVATIVE; 2,3 BIS(4 DODECYLOXYPHENYL) 1,3 BUTADIENE; 2,3 BIS(4 FLUORYPHENYL) 1,3 BUTADIENE; 2,3 DI(2 THIENYL) 1,3 BUTADIENE; 2,3 DIARYL 1,3 BUTADIENE DERIVATIVE; 2,3 DICHLORO 1,3 BUTADIENE; 2,3 DIPHENYL 1,3 BUTADIENE; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTRON TRANSPORT; INFRARED RADIATION; PHOTOLUMINESCENCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33750510049     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.498     Document Type: Article

References (38)

1. For recent reviews, see: a) R. V. Kaberdin, V. I. Potkin, V. A. Zapol'skii, Russ. Chem. Rev. 1999, 68, 765.
2. b) A. Zapf, M. Beller, Top. Catal. 2002, 19, 101.
3. c) A. A. Vasil'ev, E. P. Serebryakov, Russ. Chem. Bull., Int. Ed. 2002, 51, 1341.
4. For recent articles, see: a) S. Fielder, D. D. Rowan, M. S. Sherburn, Angew. Chem., Int. Ed. 2000, 39, 4331.
5. b) M. R. Bryce, M. A. Coffin, P. J. Skabara, A. J. Moore, A. S. Batsanov, J. A. K. Howard, Chem. Eur. J. 2000, 6, 1955.
6. c) J. Ichikawa, M. Fujiwara, S. Miyazaki, M. Ikemoto, T. Okauchi, T. Minami, Org. Lett. 2001, 3, 2345.
7. d) D. A. Shultz, R. M. Fico, Jr., S. H. Bodner, R. K. Kumar, K. E. Vostrikova, J. W. Kampf, P. D. Boyle, J. Am. Chem. Soc. 2003, 125, 11761.
8. e) M. Klokkenburg, M. Lutz, A. L. Spek, J. H. van der Maas, C. A. van Walree, Chem. Eur. J. 2003, 9, 3544.
9. a) K. Sisido, H. Nozaki, T. Iwako, J. Am. Chem. Soc. 1949, 71, 2037.
10. b) P. J. Baldry, J. Chem. Soc., Perkin Trans. 1975, 1913.
11. c) Y. Ogata, A. Kawasaki, M. Haba, T. Tsujino, J. Org. Chem. 1977, 42, 2423.
12. d) A. Kawamoto, H. Uda, N. Harada, Bull. Chem. Soc. Jpn. 1980, 53, 3279.
13. e) T. Iwashita, M. Suzuki, T. Kusumi, H. Kakisawa, Chem. Lett. 1980, 383.
14. f) R. A. Wagner, U. H. Brinker, Synthesis 2001, 376.
15. L. Engman, S. E. Byström, J. Org. Chem. 1985, 50, 3170.
16. P.-H. Lee, D. Seomoon, K. Lee, Org. Lett. 2005, 7, 343.
17. J. Böhmer, R. Grigg, Tetrahedron 1999, 55, 13463.
18. M. Shimizu, T. Kurahashi, T. Hiyama, Synlett 2001, 1006.
19. T. Takahashi, Z. Xi, R. Fischer, S. Huo, C. Xi, K. Nakajima, J. Am. Chem. Soc. 1997, 119, 4561.
20. J. Nakayama, H. Machida, R. Saito, Chem. Lett. 1985, 1173.
21. Y. Ishiono, I. Nishiguchi, F. Takihira, T. Hirashita, Tetrahedron Lett. 1980, 21, 1527.
22. P. R. Johnson, Rubber Chem. Technol. 1976, 49, 650.
23. a) K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374.
24. b) K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S.-i. Kodama, I. Nakajima, A. Minato, M. Kumada, Bull. Chem. Soc. Jpn. 1976, 49, 1958.
25. For recent reviews, see: a) V. A. Pavlov, Usp. Khim. 2001, 70, 1175.
26. b) A. Yamamoto, J. Organomet. Chem. 2002, 635, 5.
27. c) K. Tamao, J. Organomet. Chem. 2002, 653, 23.
28. d) T. Hayashi, J. Organomet. Chem. 2002, 653, 41.
29. e) M. R. Netherton, G. C. Fu, Adv. Synth. Catal. 2004, 346, 1525.
30. For recent articles, see: a) E. Mena-Osteritz, A. Meyer, B. M. W. Langeveld-Voss, R. A. J. Janssen, E. W. Meijer, P. Bäuerle, Angew. Chem., Int. Ed. 2000, 39, 2680.
31. b) K. Naka, T. Uemura, Y. Chujo, Macromolecules 2002, 35, 3539.
32. c) T. Yamamoto, Y. Muramatsu, B.-L. Lee, H. Kokubo, S. Sasaki, M. Hasegawa, T. Yagi, K. Kubota, Chem. Mater. 2003, 15, 4384.
33. d) J. E. Gano, D. J. Osborn, III, N. Kodali, P. Sekher, M. Liu, E. D. Luzik, Jr., J. Org. Chem. 2003, 68, 3710.
34. e) Z. Wu, S. Wu, Y. Liang, Spectrochim. Acta, Part A 2003, 59, 1631.
35. f) M. Surin, E. Hennebicq, C. Ego, D. Marsitzky, A. C. Grimsdale, K. Müllen, J.-L. Brédas, R. Lazzaroni, P. Leclére, Chem. Mater. 2004, 16, 994.
36. g) J. E. Klare, G. S. Tulevski, K. Sugo, A. de Picciotto, K. A. White, C. Nuckolls, J. Am. Chem. Soc. 2003, 125, 6030.
37. 2,3-Dichloro-1,3-butadiene is also handled in DuPont Performance Elastomers K.K. and Bayer Ltd.
38. I. Wurster, L. Mans, G. Kallinowski, W. Vogt, Makromol. Chem., Rapid Commun. 1984, 5, 579.