Molecular structure determination and studies on chemical and electrochemical redox reactions of a cyclic triselenide compound, 4,7-dimethoxybenzotriselenole

Heterocycles

Volumn 43, Issue 9, 1996, Pages 1843-1846

  Ogawa, Satoshi ^a   Ohmiya, Tadahito ^a   Kikuchi, Takamasa ^a   Kawai, Yasushi ^b   Niizuma, Shigeya ^a   Sato, Ryu ^a  

^a IWATE UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001100983     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7528     Document Type: Article

References (28)

1. For example, see; S. Ogawa, N. Yomoji, S. Chida, and R. Sato, Chem. Lett., 1994, 507; M. J. Plater and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1991, 317; N. Tokitoh, H. Ishizuka, A. Yabe, and W. Ando, Tetrahedron Lett., 1989, 30, 2955; B. L. Chenard, R. L. Harlow, A. L. Johnson, and S. A. Vladuchick, J. Am. Chem. Soc., 1985, 107, 3871; K. Rasheed and J. D. Warkentin, J. Org. Chem., 1980, 45, 4806.
2. For example, see; S. Ogawa, N. Yomoji, S. Chida, and R. Sato, Chem. Lett., 1994, 507; M. J. Plater and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1991, 317; N. Tokitoh, H. Ishizuka, A. Yabe, and W. Ando, Tetrahedron Lett., 1989, 30, 2955; B. L. Chenard, R. L. Harlow, A. L. Johnson, and S. A. Vladuchick, J. Am. Chem. Soc., 1985, 107, 3871; K. Rasheed and J. D. Warkentin, J. Org. Chem., 1980, 45, 4806.
3. For example, see; S. Ogawa, N. Yomoji, S. Chida, and R. Sato, Chem. Lett., 1994, 507; M. J. Plater and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1991, 317; N. Tokitoh, H. Ishizuka, A. Yabe, and W. Ando, Tetrahedron Lett., 1989, 30, 2955; B. L. Chenard, R. L. Harlow, A. L. Johnson, and S. A. Vladuchick, J. Am. Chem. Soc., 1985, 107, 3871; K. Rasheed and J. D. Warkentin, J. Org. Chem., 1980, 45, 4806.
4. For example, see; S. Ogawa, N. Yomoji, S. Chida, and R. Sato, Chem. Lett., 1994, 507; M. J. Plater and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1991, 317; N. Tokitoh, H. Ishizuka, A. Yabe, and W. Ando, Tetrahedron Lett., 1989, 30, 2955; B. L. Chenard, R. L. Harlow, A. L. Johnson, and S. A. Vladuchick, J. Am. Chem. Soc., 1985, 107, 3871; K. Rasheed and J. D. Warkentin, J. Org. Chem., 1980, 45, 4806.
5. For example, see; S. Ogawa, N. Yomoji, S. Chida, and R. Sato, Chem. Lett., 1994, 507; M. J. Plater and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1991, 317; N. Tokitoh, H. Ishizuka, A. Yabe, and W. Ando, Tetrahedron Lett., 1989, 30, 2955; B. L. Chenard, R. L. Harlow, A. L. Johnson, and S. A. Vladuchick, J. Am. Chem. Soc., 1985, 107, 3871; K. Rasheed and J. D. Warkentin, J. Org. Chem., 1980, 45, 4806.
6. M. J. Earle, K. R. Griffiths, and A. G. Massey, Polyhedron, 1992, 11, 395; R. E. Humphries and A. G. Massey, Phosphorus and Sulfur, 1988, 36, 135; N. Tokitoh, H. Ishizuka, and W. Ando, Chem. Lett., 1988, 657.
7. M. J. Earle, K. R. Griffiths, and A. G. Massey, Polyhedron, 1992, 11, 395; R. E. Humphries and A. G. Massey, Phosphorus and Sulfur, 1988, 36, 135; N. Tokitoh, H. Ishizuka, and W. Ando, Chem. Lett., 1988, 657.
8. M. J. Earle, K. R. Griffiths, and A. G. Massey, Polyhedron, 1992, 11, 395; R. E. Humphries and A. G. Massey, Phosphorus and Sulfur, 1988, 36, 135; N. Tokitoh, H. Ishizuka, and W. Ando, Chem. Lett., 1988, 657.
9. S. Ogawa, T. Kikuchi, S. Niizuma, and R. Sato, J. Chem. Soc., Chem. Comm., 1994, 1593. Two other trichalcogenolium radical cations have been reported. See; G. Wolmershäuser and G. Heckmann, Angew. Chem., Int. Ed. Engl., 1992, 31, 779; T. S. Cameron, R. C. Haddon, S. M. Mattar, S. Parsons, J. Passmore, and A. P. Ramirez, J. Chem. Soc., Dalton Trans., 1992, 1563.
10. S. Ogawa, T. Kikuchi, S. Niizuma, and R. Sato, J. Chem. Soc., Chem. Comm., 1994, 1593. Two other trichalcogenolium radical cations have been reported. See; G. Wolmershäuser and G. Heckmann, Angew. Chem., Int. Ed. Engl., 1992, 31, 779; T. S. Cameron, R. C. Haddon, S. M. Mattar, S. Parsons, J. Passmore, and A. P. Ramirez, J. Chem. Soc., Dalton Trans., 1992, 1563.
11. S. Ogawa, T. Kikuchi, S. Niizuma, and R. Sato, J. Chem. Soc., Chem. Comm., 1994, 1593. Two other trichalcogenolium radical cations have been reported. See; G. Wolmershäuser and G. Heckmann, Angew. Chem., Int. Ed. Engl., 1992, 31, 779; T. S. Cameron, R. C. Haddon, S. M. Mattar, S. Parsons, J. Passmore, and A. P. Ramirez, J. Chem. Soc., Dalton Trans., 1992, 1563.
12. Other type 5-membered 7π radical cations have been reported. See;T. S. Cameron, R. C. Haddon, S. M. Mattar, S. Parsons, J. Passmore, and A. P. Ramirez, Inorg. Chem., 1992, 31, 2274; E. G. Awere, J. Passmore, P. S. White, and T. Klapötke, J. Chem. Soc., Chem. Comm., 1989, 1415; E. G. Awere, J. Passmore, K. F. Preston, and L. H. Sutcliffe, Can. J. Chem., 1988, 66, 1776.
13. Other type 5-membered 7π radical cations have been reported. See;T. S. Cameron, R. C. Haddon, S. M. Mattar, S. Parsons, J. Passmore, and A. P. Ramirez, Inorg. Chem., 1992, 31, 2274; E. G. Awere, J. Passmore, P. S. White, and T. Klapötke, J. Chem. Soc., Chem. Comm., 1989, 1415; E. G. Awere, J. Passmore, K. F. Preston, and L. H. Sutcliffe, Can. J. Chem., 1988, 66, 1776.
14. Other type 5-membered 7π radical cations have been reported. See;T. S. Cameron, R. C. Haddon, S. M. Mattar, S. Parsons, J. Passmore, and A. P. Ramirez, Inorg. Chem., 1992, 31, 2274; E. G. Awere, J. Passmore, P. S. White, and T. Klapötke, J. Chem. Soc., Chem. Comm., 1989, 1415; E. G. Awere, J. Passmore, K. F. Preston, and L. H. Sutcliffe, Can. J. Chem., 1988, 66, 1776.
15. S. Ogawa, T. Kikuchi, A. Sasaki, S. Chida, and R. Sato, Tetrahedron Lett., 1994, 35, 5469.
16. 2Sn: C, 27.12; H, 3.19. Found: C, 27.13; H, 3.40.
17. 3: C, 25.76; H, 2.16. Found: C, 25.94; H, 2.14.
18. -1 (in ω), scan width=(1.42 + 0.30 tanθ)°, and CuKα radiation (λ=1.54178Å). The structure was solved by heavy-atom Patterson methods (PATTY) and expanded using Fourier techniques (DIRDIF92). All calculations were performed using the teXsan crystallographic software package. The final cycle of full-matrix least-square refinement was based on 2095 observed reflections (I>3.00σ(I)) and 300 variable parameters with R=0.066, Rw=0.076.
19. M. J. Potrzebowski, M. Michalska, J. Blaszczyk, M. W. Wieczorek, W. Ciesielski, S. Kazmierski, and J. Pluskowski, J. Org. Chem., 1995, 60, 3139; P. J. Barrie and R. J. H. Clark, Inorg. Chem., 1995, 34, 4299; J. J. Ellison, K. Ruhlandt-Senge, H. H. Hope, and P. P. Power, ibid., 1995, 34, 49; M. Iwaoka and S. Tomoda, Phosphorus, Sulfur, and Silicon, 1992, 6 7, 125.
20. M. J. Potrzebowski, M. Michalska, J. Blaszczyk, M. W. Wieczorek, W. Ciesielski, S. Kazmierski, and J. Pluskowski, J. Org. Chem., 1995, 60, 3139; P. J. Barrie and R. J. H. Clark, Inorg. Chem., 1995, 34, 4299; J. J. Ellison, K. Ruhlandt-Senge, H. H. Hope, and P. P. Power, ibid., 1995, 34, 49; M. Iwaoka and S. Tomoda, Phosphorus, Sulfur, and Silicon, 1992, 6 7, 125.
21. M. J. Potrzebowski, M. Michalska, J. Blaszczyk, M. W. Wieczorek, W. Ciesielski, S. Kazmierski, and J. Pluskowski, J. Org. Chem., 1995, 60, 3139; P. J. Barrie and R. J. H. Clark, Inorg. Chem., 1995, 34, 4299; J. J. Ellison, K. Ruhlandt-Senge, H. H. Hope, and P. P. Power, ibid., 1995, 34, 49; M. Iwaoka and S. Tomoda, Phosphorus, Sulfur, and Silicon, 1992, 6 7, 125.
22. M. J. Potrzebowski, M. Michalska, J. Blaszczyk, M. W. Wieczorek, W. Ciesielski, S. Kazmierski, and J. Pluskowski, J. Org. Chem., 1995, 60, 3139; P. J. Barrie and R. J. H. Clark, Inorg. Chem., 1995, 34, 4299; J. J. Ellison, K. Ruhlandt-Senge, H. H. Hope, and P. P. Power, ibid., 1995, 34, 49; M. Iwaoka and S. Tomoda, Phosphorus, Sulfur, and Silicon, 1992, 6 7, 125.
23. 3 as a reference electrode, scan rate 50-500 mV/s.
24. H. Fujihara, Y. Higuchi, H. Mima, and N. Furukawa, Chem. Lett., 1994, 619; H. Fujihara, M. Yabe, M. Ikemori, and N. Furukawa, J. Chem. Soc., Perkin Trans. 1, 1993, 2145; H. Fujihara, Y. Ueno, J. J. Chiu, and N. Furukawa, Chem. Lett., 1991, 1649; H. Fujihara, R. Akaishi, and N. Furukawa, ibid., 1990, 549.
25. H. Fujihara, Y. Higuchi, H. Mima, and N. Furukawa, Chem. Lett., 1994, 619; H. Fujihara, M. Yabe, M. Ikemori, and N. Furukawa, J. Chem. Soc., Perkin Trans. 1, 1993, 2145; H. Fujihara, Y. Ueno, J. J. Chiu, and N. Furukawa, Chem. Lett., 1991, 1649; H. Fujihara, R. Akaishi, and N. Furukawa, ibid., 1990, 549.
26. H. Fujihara, Y. Higuchi, H. Mima, and N. Furukawa, Chem. Lett., 1994, 619; H. Fujihara, M. Yabe, M. Ikemori, and N. Furukawa, J. Chem. Soc., Perkin Trans. 1, 1993, 2145; H. Fujihara, Y. Ueno, J. J. Chiu, and N. Furukawa, Chem. Lett., 1991, 1649; H. Fujihara, R. Akaishi, and N. Furukawa, ibid., 1990, 549.
27. H. Fujihara, Y. Higuchi, H. Mima, and N. Furukawa, Chem. Lett., 1994, 619; H. Fujihara, M. Yabe, M. Ikemori, and N. Furukawa, J. Chem. Soc., Perkin Trans. 1, 1993, 2145; H. Fujihara, Y. Ueno, J. J. Chiu, and N. Furukawa, Chem. Lett., 1991, 1649; H. Fujihara, R. Akaishi, and N. Furukawa, ibid., 1990, 549.
28. 3: C, 18.55; H, 1.56. Found: C, 18.84; H, 1.51.