Reactions of (1R,2S)-1,2-di(2-furyl)-1,2-di(3-guaiazulenyl)ethane and (1R,2S)-1,2-di(3-guaiazulenyl)-1,2-di(2-thienyl)ethane with tetracyanoethylene (TCNE) in benzene: Comparative studies on the products and their spectroscopic properties

Tetrahedron

Volumn 62, Issue 7, 2006, Pages 1520-1526

  Takekuma, Shin Ichi ^a   Takahashi, Kenji ^a   Sakaguchi, Akio ^a   Sasaki, Masato ^a   Minematsu, Toshie ^a   Takekuma, Hideko ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

Annulation; C C bond cleavage; Charge transfer complex; Furan; Guaiazulene; TCNE; Thiophene; X ray crystal structure

Indexed keywords

1,2 DI(2 FURYL) 1,2 DI(3 GUAIAZULENYL)ETHANE; 1,2 DI(3 GUAIAZULENYL) 1,2 DI(2 THIENYL)ETHANE; 2,2,3,3 TETRACYANO 4 (2 FURYL) 8 ISOPROPYL 6 METHYL 1,4 DIHYDROCYCLOHEPTA[C,D]AZULENE; 2,2,3,3 TETRACYANO 8 ISOPROPYL 6 METHYL 4 (2 THIENYL) 1,4 DIHYDROCYCLOHEPTA[C,D]AZULENE; AZULENE DERIVATIVE; BENZENE; GUAIAZULENE; TETRACYANOETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPARATIVE STUDY; PRIORITY JOURNAL; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 30744456754     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.026     Document Type: Article

References (26)

1. S. Takekuma, M. Sasaki, H. Takekuma, and H. Yamamoto Chem. Lett. 1999 999 1000
2. S. Takekuma, S. Takata, M. Sasaki, and H. Takekuma Tetrahedron Lett. 42 2001 5921 5924
3. S. Takekuma, M. Tanizawa, M. Sasaki, T. Matsumoto, and H. Takekuma Tetrahedron Lett. 43 2002 2073 2078
4. M. Sasaki, M. Nakamura, G. Hannita, H. Takekuma, T. Minematsu, M. Yoshihara, and S. Takekuma Tetrahedron Lett. 44 2003 275 279
5. M. Sasaki, M. Nakamura, T. Uriu, H. Takekuma, T. Minematsu, M. Yoshihara, and S. Takekuma Tetrahedron 59 2003 505 516
6. M. Nakamura, M. Sasaki, H. Takekuma, T. Minematsu, and S. Takekuma Bull. Chem. Soc. Jpn. 76 2003 2051 2052
7. S. Takekuma, K. Sasaki, M. Nakatsuji, M. Sasaki, T. Minematsu, and H. Takekuma Bull. Chem. Soc. Jpn. 77 2004 379 380
8. M. Nakatsuji, Y. Hata, T. Fujihara, K. Yamamoto, M. Sasaki, H. Takekuma, M. Yoshihara, T. Minematsu, and S. Takekuma Tetrahedron 60 2004 5983 6000
9. S. Takekuma, Y. Hata, T. Nishimoto, E. Nomura, M. Sasaki, T. Minematsu, and H. Takekuma Tetrahedron 61 2005 6892 6907
10. S. Takekuma, K. Takahashi, A. Sakaguchi, Y. Shibata, M. Sasaki, T. Minematsu, and H. Takekuma Tetrahedron 61 2005 10349 10362
11. 2 under the same electrochemical conditions as 1.
12. The cyclic and differential pulse voltammograms of 2 (3.0 mg, 5.1 μmol) were measured under the same electrochemical conditions as 1.
13. 3CN under the same electrochemical conditions as TCNE.
14. K. Hafner, and K.-L. Moritz Liebigs Ann. Chem. 650 1961 92 97
15. A.J. Fatiadi Synthesis 1986 249 284
16. A.J. Fatiadi Synthesis 1987 749 789
17. P. Bruni, and G. Tosi Gazz. Chim. Ital. 127 1997 435 459
18. O.W. Webster J. Polym. Sci., Part A: Polym.Chem. 40 2002 210 221
19. A. Flamini Curr. Org. Chem. 7 2003 1793 1820
20. P. Clements, G.E. Gream, P.K. Kirkbride, and S.M. Pyke Helv. Chim. Acta 88 2005 2003 2021
21. J.R. Roland, and B.C. McKusick J. Am. Chem. Soc. 83 1961 1652 1657
22. L.T. Scott, and M.A. Kirms J. Am. Chem. Soc. 104 1982 3530 3531
23. S. Balduzzi, H. Mueller-Bunz, and M.J. McGlinchey Chem. Eur. J. 10 2004 5398 5405
24. +, m/z 555.3263.
25. +, m/z 715.2929.
26. S. Takekuma, Y. Matsubara, H. Yamamoto, and T. Nozoe Bull. Chem. Soc. Jpn. 61 1988 475 481