Electrochemical reduction of pyrrole in the presence of trinitrofluorenone: Isolation of a Meisenheimer complex

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4572-4573

  Hoshino, Katsuyoshi ^a   Ozawa, Nobuo ^a   Kokado, Hiroshi ^a   Seki, Hiroko ^a   Tokunaga, Tatsuhiro ^a   Ishikawa, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENONE DERIVATIVE; NITROGEN; POLYPYRROLE; PYRROLE DERIVATIVE; SODIUM PERCHLORATE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTRIC CURRENT; ELECTROCHEMICAL ANALYSIS; ELECTROCHEMISTRY; OXIDATION; POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY;

EID: 0033603362     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904361     Document Type: Article

References (25)

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4. Gill, W. D. J. Appl. Phys. 1972, 43, 5033-5040.
5. 2 column chromatography to give 3.
6. Characterization of the new film will be discussed elswhere.
7. 1/2 in DMSO and in MeOH at 20°C were estimated to be 10 and 4 h, respectively, by the same experiment. A powder of 3 could be stored without decomposition at 0°C in an inert atomosphere.
8. 3CN was used as a solvent for preparation of samples for measurement. The expected peak due to a molecular ion could not be observed in the FABMS of 3.
9. Separation of the isomeric products has not been achieved to date.
10. (a) Halle, J. C.; Terrier, F.; Pouet, M. J.; Simonnin, M. P. J. Chem. Res. (S) 1980, 360-361.
11. (b) Sepuleri, P.; Goumont, R.; Halle, J.-C.; Buncel, E.; Terrier, F. J. Chem. Soc., Chem. Commun. 1987, 789-790.
12. 4α)].
13. 2-N in the minor isomer 3b was observed.
14. 2O was referenced to 0 ppm as an external standard.
15. 2O: C, 48.96; H, 3.31; N, 12.11; Na, 4.97).
16. Although attempts to isolate these adducts failed due to their instabilities, successive electro-oxidation under the same condition as with adduct 3 afforded the corresponding new films. Their characterization will be discussed elswhere.
17. 2 will permeate into a cathode compartment from the anode compartment through a sintered glass filter during extended periods of electrolysis even under a nitrogen atmosphere.
18. 2-.
19. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, p 715.
20. Hydroperoxide anion may be scavenged by other species including the solvent.
21. Loutfy, R. O.; Hsiao, C. K.; Ong, B. S.; Keoshkerian, B. Can. J. Chem. 1984, 62, 1877-1885.
22. (a) Strauss, M. J. Chem. Rev. 1970, 70, 667-712.
23. (b) Terrier, F. Ibid. 1982, 82, 77-152.
24. (c) Artamkina, G. A.; Egorov, M. P.; Beletskaya, I. P. Ibid. 1982, 82, 427-459.
25. 9b The π-complex was shown to rapidly give rise to the corresponding σ-complexes, when it was placed in DMSO. The authors pointed out the important role of an increased charge density of an indole nucleus by substitution of a carboxylate ion at the 3 position for these complex formations.