Electrochemistry of 1,3-diazadihydroazulanone: Electrochemical reduction and oxidation of 1-tosyl-3-aryl-1,3-diazadihydroazulanone leading to migration and elimination of the tosyl group

Heterocycles

Volumn 53, Issue 3, 2000, Pages 519-524

  Saito, Katsuhiro ^a   Ido, Takayasu ^a   Awadu, Yasutaka ^a   Kanie, Takashi ^a   Kondo, Satoru ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; MOLECULAR DYNAMICS; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0034162274     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-8749     Document Type: Article

References (18)

1. W. E. Stewart and T. H. Siddall, Chem. Rev., 1970, 70, 517; T. Sato, Y. Fukazawa, Y. Fujise, and S. Ito, Heterocycles, 1977, 7, 807.
2. W. E. Stewart and T. H. Siddall, Chem. Rev., 1970, 70, 517; T. Sato, Y. Fukazawa, Y. Fujise, and S. Ito, Heterocycles, 1977, 7, 807.
3. K. Ito, K. Saito, and K. Takahashi, Bull. Chem. Soc. Jpn, 1992, 65, 812; M. Nitta, H. Tomioka, A. Akaogi, K. Takahashi, K. Saito, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1994, 2625; K. Ito and K. Saito, Bull. Chem. Soc. Jpn., 1995, 68, 3539.
4. K. Ito, K. Saito, and K. Takahashi, Bull. Chem. Soc. Jpn, 1992, 65, 812; M. Nitta, H. Tomioka, A. Akaogi, K. Takahashi, K. Saito, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1994, 2625; K. Ito and K. Saito, Bull. Chem. Soc. Jpn., 1995, 68, 3539.
5. K. Ito, K. Saito, and K. Takahashi, Bull. Chem. Soc. Jpn, 1992, 65, 812; M. Nitta, H. Tomioka, A. Akaogi, K. Takahashi, K. Saito, and K. Ito, J. Chem. Soc., Perkin Trans. 1, 1994, 2625; K. Ito and K. Saito, Bull. Chem. Soc. Jpn., 1995, 68, 3539.
6. K. Ito and K. Saito, Heterocycles, 1994, 38, 2691; idem, ibid, 1995, 41, 2307.
7. K. Ito and K. Saito, Heterocycles, 1994, 38, 2691; idem, ibid, 1995, 41, 2307.
8. K. Saito, M. Hattori, T. Sato, and K. Takahashi, Heterocycles, 1992, 34, 129; S. Kondo, H. Suzuki, T. Hattori, T. Ido, and K. Saito, ibid., 1998, 48, 1151.
9. K. Saito, M. Hattori, T. Sato, and K. Takahashi, Heterocycles, 1992, 34, 129; S. Kondo, H. Suzuki, T. Hattori, T. Ido, and K. Saito, ibid., 1998, 48, 1151.
10. -1.
11. b, of the following compound are observed to be 6.12 ppm. T. Ido, A Thesis for a Masterate, Nagoya Inst. Tech., 1998. (equation)
12. 3) δ ppm 4.19 (1H, bs), 5.16 (1H, dd, J = 9.9 and 3.3 Hz), 5.59 (1H d, J = 6.6 Hz), 6.14 (1H, dd, J = 6.3 and 9.9 Hz), 6.27 (1H, dd, J = 11.0 and 6.3 Hz), 6.45 (1H, dd, J = 6.6 and 11.0 Hz), 7.26 (2H d, J = 8.5 Hz), 7.58 (2H, d, J = 8.5 Hz).
13. K. Sanechika, S. Kajigaeshi, and S Kanemasa, Chem. Lett., 1977, 861; K. Ito, K. Saito, and K. Takahashi, Heterocycles, 1991, 32, 1117; K. Ito, Y. Hara, R. Sakakibara, and K. Saito, ibid., 1995, 41, 1675.
14. K. Sanechika, S. Kajigaeshi, and S Kanemasa, Chem. Lett., 1977, 861; K. Ito, K. Saito, and K. Takahashi, Heterocycles, 1991, 32, 1117; K. Ito, Y. Hara, R. Sakakibara, and K. Saito, ibid., 1995, 41, 1675.
15. K. Sanechika, S. Kajigaeshi, and S Kanemasa, Chem. Lett., 1977, 861; K. Ito, K. Saito, and K. Takahashi, Heterocycles, 1991, 32, 1117; K. Ito, Y. Hara, R. Sakakibara, and K. Saito, ibid., 1995, 41, 1675.
16. The authors are indebted to Prof. Yoshiro Yamashita of the Institute for Molecular Science for his measurements of cyclic voltammetries.
17. The maximum value of the free valencies appears at 4-position. However the attack of the tosyll group at the 4-position of 11 seems to be avoided because of the steric hindrance caused by the adjacent aryl group.
18. A mechanism which affords 3 directly from 9, seems to be still possible. The researches on the detailed reaction mechanism are now in progress.