Phenyl substitution effects on rate acceleration of cation radical deazetation of 2,3-diazabicyclo[2.2.2] oct-2-enes

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4377-4380

  Ikeda, Hiroshi ^a   Minegishi, Tomonori ^a   Takahashi, Yasutake ^a   Miyashi, Tsutomu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 2,3 DIAZABICYCLO[2.2.2]OCT 2 ENE; 1,4 DIPHENYL 2,3 DIAZABICYCLO[2.2.2]OCT 2 ENE; 2,3 DIAZABICYCLO[2.2.2]OCT 2 ENE; ANTHRACENE DERIVATIVE; CATION; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; ELECTRON TRANSPORT; OXIDATION REDUCTION POTENTIAL; PHOTOREACTIVITY; REACTION ANALYSIS;

EID: 0029934592     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00855-6     Document Type: Article

References (24)

1. Ikeda, H.; Minegishi, T.; Miyashi, T, J. Chem. Soc., Chem. Commun., 1994, 297-298.
2. Adam, W.; Grabowski, S.; Miranda, M. A.; Rübenacker, M. J. Chem. Soc., Chem. Commun., 1988, 142-143.
3. Williams, F.; Guo, Q.-X.; Petillo, P. A.; Nelsen, S. F. J. Am. Chem. Soc. 1988, 110, 7887-7888.
4. Blackstock, S. C.; Kochi, J. K. J. Am. Chem. Soc. 1987, 109, 2484-2496.
5. Engel, P. S.; Robertson, D. M.; Scholz, J. N.; Shine, H. J. J. Org. Chem. 1992, 57, 6178-6187.
6. Engel, P. S.; Kitamura, A.; Keys, D. E. J. Org. Chem. 1987, 52, 5015-5021.
7. 4 as a supporting electrolyte.
8. A 0.5 mL solution was irradiated with a 2 kW Xe lamp through a cutoff filter (λ > 410 nm) at 20 °C.
9. 3); δppm 24.97 (2 C), 34.56 (2 C), 40.30, 49.11, 124.68 (2 C), 125.28, 128.19 (2 C), 148.68.
10. -3 M. Aberchrome 540 was used as an actinometer.
11. Kitamura and coworkers pointed out the importance of BET in CR deazetations: (a) Karatsu, T.; Itoh, H.; Kikunaga, T.; Ebashi, Y.; Hotta, H.; Kitamura, A. J. Org. Chem., 1995, 60, 8270-8277.
12. (b) Karatsu, T.; Ichino, Y.; Kitamura, A.; Owens, W. H.; Engel, P. S. J. Chem. Res. (S), 1995, 440-441.
13. 4--Moluene cosensitized conditions (λ = 305 ± 5 nm).
14. Olah, G. A.; Pittman Jr., C. U.; Waack, R.; Doran, M. J. Am. Chem. Soc., 1966, 88, 1488-1495.
15. Boate, D. R.; Scaiano, J. C. Tetrahedron Lett., 1989, 30, 4633-4636.
16. 17, 18 Formula presented
17. (a) Miller, J. R.; Beitz, J. V.; Huddleston, R. K. J. Am. Chem. Soc., 1984, 106, 5057-5068.
18. (b) Siders, P.; Marcus, R. A. J. Am. Chem. Soc., 1981, 103, 741-747, 748-752.
19. (c) Van Duyne, R. P.; Fischer, S. F. Chem. Phys. 1974, 5, 183-197.
20. (d) Ulstrup, J.; Jortner, J. J. Chem. Phys., 1975, 63, 4358-4368.
21. Niwa, T.; Kikuchi, K.; Matsushita, N.; Hayashi, M.; Katagiri, T.; Takahashi, Y.; Miyashi, T. J. Phys. Chem. 1993, 97, 11960-11964.
22. 2/εr = 0.23 eV.
23. Engel, P. S.; Nalepa, C. J.; Horsey, D. W.; Keys, D. E.; Grow, R. T. J. Am. Chem. Soc., 1983, 105, 7102-7107, and references cited therein.
24. PM3 calculations were carried out by using the MOPAC ver. 6 on a Tektronix CAChe WorkSystem.