McMurry coupling of diformyldithienylacetylene: Synthesis of [24]-, [36]-, and [48]annulenes composed of thiophene, acetylene, and ethylene units

Heterocycles

Volumn 82, Issue 2, 2010, Pages 1143-1149

  Iyoda, Masahiko ^a   Huang, Pochi ^a   Nishiuchi, Tomohiko ^a   Takase, Masayoshi ^a   Nishinaga, Tohru ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952748096     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)96     Document Type: Article

References (31)

1. Carbon-Rich Compounds, From Molecules to Materials, eds. by M. H. Haley and R. R Tykwinski, Wiley-VCH, Weinheim, 2006
2. (b) J. Wu, W. Pisula, and K. Müllen, Chem. Rev., 2007, 107, 718.
3. For recent reviews of π-conjugated macrocycles, see: (a) Modern Supramolecular Chemistry: Strategies for Macrocycle Synthesis, eds. by F. Diederich, P. J. Stang, and R. R. Tykwinski, Wiley-VCH, Weinheim, 2008
4. (b) T. Kawase, Synlett, 2007, 2609.
5. (c) W. Zhang and J. S. Moore, Adv. Synth. Catal., 2007, 349, 93
6. (d) K. Tahara and Y. Tobe, Chem. Rev., 2006, 106, 5274
7. (e) E. L. Spitler, C. A. Johnson II, and M. M. Haley, Chem. Rev., 2006, 106, 5344
8. (f) S. Höger, Angew. Chem. Int. Ed., 2005, 44, 3806
9. (g) Y. Yamaguchi and Z. Yoshida, Chem. Eur. J., 2003, 9, 5430
10. (h) C. Grave and A. D. Schlüter, Eur. J. Org. Chem., 2002, 3075.
11. (a) J.-Y. Shin, K. S. Kim, M.-C. Yoon, J. M. Lim, Z. S. Yoon, A. Osuka, and D. Kim, Chem. Soc. Rev., 2010, 39, 2751
12. (b) M. Hasegawa and M. Iyoda, Chem. Soc. Rev., 2010, 39, 2420
13. (c) P. J. Chmielewski, Angew. Chem. Int. Ed., 2010, 49, 1359.
14. T. Kawase, H. R. Darabi, R. Uchimiya, and M. Oda, Chem. Lett., 1995, 499.
15. (a) K. Nakao, M. Nishimura, T. Tamachi, Y. Kuwatani, H. Miyasaka, T. Nishinaga, and M. Iyoda, J. Am. Chem. Soc., 2006, 128, 16740.
16. (b) M. Williams-Harry, A. Bhaskar, G. Ramakrishna, T. Goodson, III, M. Imamura, A. Mawatari, K. Nakao, H. Enozawa, T. Nishinaga, and M. Iyoda, J. Am. Chem. Soc., 2008, 130, 3252.
17. (a) M. Iyoda, Pure Appl. Chem., 2010, 82, 831
18. (b) M. Iyoda, Comptes Rendus Chimie, 2009, 12, 395
19. (c) M. Iyoda, M. Hasegawa, and H. Enozawa, Chem. Lett., 2007, 36, 1402
20. (d) M. Iyoda, Heteroatom Chem., 2007, 18, 460.
21. Z. Hu, J. L. Atwood, and M. P. Cava, J. Org. Chem., 1994, 59, 8071.
22. 9 with n-BuLi (2.75 equiv.) at 0 °C and DMF (2.9 equiv.) in the temperature range from 0 °C to room temperature.
23. C. Ringenbach, A. De Nicola, and R. Ziessel, J. Org. Chem., 2003, 68, 4708.
24. +).
25. +). Chemical equation presented.
26. 1 = 0.0796, Rw = 0.1854, GOF = 1.060. Among a total of 11150 reflections measured, 3752 were unique, and the observed (I > 2.00σ(I )) 2948 reflections were used for the refinement. The crystal structure was solved by using the SHELXS-97 program and refined by using the full matrix least-squares method in the SHELXS-97 software package. Cambridge Crystallographic Data Centre deposition No. CCDC-752997.
27. The most stable diastereomers of 2b and 3b are all-Z-and E,Z,E,Z-isomers, respectively, on the basis of MO calculations at the B3LYP/6-31G(d) level.
28. F = 0.546).
29. 6 as a supporting electrolyte.
30. 4 Since the S S interatomic distances are 3.014 and 3.024 Å, which are 18.3% and 18.5% shorter than the sum of van der Waals radii (3.7 Å) respectively, the distances are too short to stabilize the structure. However, the π-π stacking interactions in the crystal may stabilize the planar structure.
31. HOMOs of 1a on the basis of MO calculations at the B3LYP/6-31G(d) level are as follows: Chemical equation presented.