Selective [2+2+2] cycloaddition of nickel-benzyne and an asymmetric 1,3-diyne: An iterative route to substituted [n]acenes

Synthesis

Volumn , Issue 18, 2004, Pages 3084-3088

  Deaton, Kimberly R ^a   Strouse, Christopher S ^a   Gin, Mary S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Alkynes; Cycloaddition; Fused ring systems; Nickel; Regioselectivity

Indexed keywords

MOLECULAR STRUCTURE; NICKEL; OLEFINS; SUBSTITUTION REACTIONS;

CYCLOADDITION; FUSED AROMATIC RINGS; NICKEL-BENZYNE;

ORGANOMETALLICS;

1 TRIMETHYLSILYL 1,3 PENTADIYNE; BICKEL BENZYNE; NICKEL COMPLEX; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 11144285384     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834894     Document Type: Article

References (36)

1. (a) Tamura, M.; Gao, D.; Ueno, A. Chem.-Eur. J. 2001, 7, 1390.
2. (b) Wang, X.; Levy, D. H.; Rubin, M. B.; Speiser, S. J. Phys. Chem. 2000, 104, 6558.
3. (a) Isaev, R. N.; Ishkov, A. V.; Fisenko, O. V. J. Anal. Chem. 2001, 56, 1095.
4. (b) Hanhela, P. J.; Paul, D. B. Aust. J. Chem. 1981, 54, 1687.
5. (a) Wurthner, F. Angew. Chem. Int. Ed. 2001, 40, 1037.
6. (b) Gundlach, D. J.; Nichols, J. A.; Zhou, L.; Jackson, T. N. Appl. Phys. Lett. 2002, 80, 2925.
7. (c) Halik, M.; Klauk, H.; Zschieschang, U.; Kriem, T.; Schmid, G.; Radlik, W.; Wussow, K. Appl. Phys. Lett. 2002, 81, 289.
8. (d) Shtein, M.; Mapel, J.; Benziger, J. B.; Forrest, S. R. Appl. Phys. Lett. 2002, 81, 268.
9. (e) Kane, M. G.; Campi, J.; Hammond, M. S.; Cuomo, F. P.; Greening, B.; Sheraw, C. D.; Nichols, J. A.; Gundlach, D. J.; Huang, J. R.; Kuo, C. C.; Jia, L.; Klauk, H.; Jackson, T. N. IEEE Electron Device Lett. 2000, 21, 534.
10. Park, S. P.; Kim, S. S.; Kim, J. H.; Whang, C. N.; Im, S. Appl. Phys. Lett. 2002, 80, 2872.
11. (a) Hegmann, F. A.; Tykwinski, R. R.; Lui, K. P. H.; Bullock, J. E.; Anthony, J. E. Phys. Rev. Lett. 2002, 89, 7403.
12. (b) Tokumoto, T.; Brooks, J. S.; Clinite, R.; Wei, X.; Anthony, J. E.; Eaton, D. L.; Parkin, S. R. J. Appl. Phys. 2002, 92, 5208.
13. (a) Houk, K. N.; Lee, P. S.; Nendel, M. J. Org. Chem. 2001, 66, 5517.
14. (b) Whangbo, M.-H.; Hoffman, R.; Woodward, R. B. Proc. R. Soc. London, Ser. A 1979, 366, 23.
15. (c) Pomerantz, M.; Cardona, R.; Rooney, P. Macromolecules 1989, 22, 304.
16. (d) Kao, J.; Lilly, A. C. Jr. J. Am. Chem. Soc. 1987, 109, 4149.
17. (e) Lowe, J. P.; Kafafi, S. A.; LaFemina, J. P. J. Phys. Chem. 1986, 90, 6602.
18. (f) Tanaka, K.; Ohzeki, K.; Nankai, S.; Yamabe, T.; Shirakawa, H. J. Phys. Chem. Solids 1983, 44, 1069.
19. (g) Kertesz, M.; Hoffman, R. Solid State Commun. 1983, 47, 97.
20. (h) Bredas, J. L.; Chance, R. R.; Baughman, R. H.; Silbey, R. J. Chem. Phys. 1982, 76, 3673.
21. (a) Kojima, Y.; Tsuji, M.; Matsuoka, T.; Takahashi, H. Macromoleculees 1994, 27, 3735.
22. (b) Snow, A. W. Nature (London) 1981, 292, 40.
23. (c) Teyssie, P.; Korn-Girard, A. C. J. Polym. Sci., Part A 1964, 2, 2849.
24. Bailey, W. J.; Liao, C.-W. J. Am. Chem. Soc. 1955, 77, 992.
25. (a) Miller, G. P.; Briggs, J. Org. Lett. 2003, 5, 4203.
26. (b) Ashton, P. R.; Brown, G. R.; Smith, D. R.; Stoddart, J. F.; Williams, D. J. Tetrahedron Lett. 1993, 34, 8337.
27. (c) Bender, D.; Mullen, K. Chem. Ber. 1988, 121, 1187.
28. (d) Hart, H.; Lai, C.-Y.; Nwokogu, G. C.; Shamouilian, S. Tetrahedron 1987, 43, 5203.
29. Bowles, D. M.; Anthony, J. E. Org. Lett. 2000, 2, 85.
30. Takahashi, T.; Kitamura, M.; Shen, B.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 12876.
31. Deaton, K. R.; Gin, M. S. Org. Lett. 2003, 5, 2477.
32. Holmes, A. B.; Jones, G. E. Tetrahedron Lett. 1980, 21, 3111.
33. Bowles, D. M.; Palmer, G. J.; Landis, C. A.; Scott, J. L.; Anthony, J. E. Tetrahedron 2001, 57, 3753.
34. Bennett, M. A.; Wenger, E. Organometallics 1995, 14, 1267.
35. Bennett, M. A.; Wenger, E. Organometallics 1996, 15, 5536.
36. Tanaka, K.; Miura, T.; Umezawa, N.; Urano, Y.; Kikuchi, K.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2001, 123, 2530.