Reaction of substituted anthracenes and a butadiene with nitric oxide: Product formation determined by EPR spectroscopy

Free Radical Research

Volumn 27, Issue 4, 1997, Pages 377-388

  Pfeiler, Dietmar ^c   Grice, I Darren ^c   Bottle, Steven E ^a   Hanson, Graeme R ^b  

^a QUEENSLAND UNIVERSITY OF TECHNOLOGY   (Australia)

^b UNIVERSITY OF QUEENSLAND   (Australia)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE; ANTHRACENE DERIVATIVE; NITRIC OXIDE; NITROSO DERIVATIVE;

ARTICLE; ELECTRON SPIN RESONANCE;

EID: 0031446310     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769709065777     Document Type: Article

References (33)

1. Moncada, S., Palmer, R. M. J. and Higgs, E. A. (1991). Nitric Oxide: Physiology, Pathophysiology, and Pharmacology. Pharmacological Reviews, 43, 109-142.
2. Culotta, E. and Koshland, D. E. (1992). NO News is Good News. Science, 258, 1862-1865.
3. Palmer, R. M. J., Ashton, D. S. and Moncada, S. (1988). Vascular Endothelial Cells Synthesize NO From L-Arginine. Nature, 333, 664-666.
4. Morletta, M. A., Yoon, P. S., Iyengar, R., Leaf, C. D. and Wishnok, J. S. (1988). Macrophage Oxidation Of L-Arginine To Nitrite And Nitrate: NO Is An Intermediate. Biochemistry, 1988, 27, 8706-8711.
5. Palmer, R. M. J., Moncada, S. and Radomski, M. W. (1987). Comparative Pharmacology Of EDRF, NO And Prostacyclin In Platelets. British Journal of Pharmacology, 92, 181-187.
6. Archer, S. (1993). Measurement Of NO In Biological Models. Federation of American Societies for Experimental Biology Journal, 7, 349-360.
7. Downes, M. J., Edwards, W., Elsey, T. S. and Walters, C. C. (1976). Determination Of A Nonvolatile Nitrosamine Using Denitrosation And A Chemiluminescence Analyser. Analyst, 101, 742-748.
8. Ignarro, L. J., Buya, G. M., Wood, K. S., Byrns, R. E. and Chaudhuri, G. (1987). EDRF Produced And Relaxed From Artery And Vein Is NO. Proceedings of the National Academy of Sciences, USA, 84, 9265-9269.
9. Greenberg, S. S., Wilcox, D. E. and Rubanyi, G. M. (1990). EDRF Released From Canine Femoval Artery Cannot Be Identified As Free NO By EPR. Circulation Research, 67, 1446-1452.
10. Quaresima, V., Takehara, H., Tsushima, K., Ferrari, M. and Utsumi, H. (1996). In Vivo Detection Of Mouse Liver NO Generation By Spin Trapping EPR. Biochemical and Biophysical Research Communications, 221, 729-734.
11. Korth, H. G., Ingold, K. U., Sustmann, R., de Groot, H. and Sies, H. (1992). Tetramethyl-Ortho-Chinodimethan (NOCT-1), Das Erste Mitglied Einer Mitglied Einer Familie Mageschneiderter Cheleotroper Spinfänger Für Stickstoffmonoxid. Angewandte Chemie, 104, 915-917.
12. Korth, H. G., Sustmann, R., Lommes, P., Paul, T., Ernst, A., de Groot, H., Hughes, L. and Ingold, K. U. (1994) NO Cheletropic Traps (NOCTS) With Improved Thermal Stability And Water Solubility, Journal of the American Chemical Society, 116, 2767-2777.
13. Gabr I. M., Rai U. S. and Symons M. C. R. (1993). Conversion of NO into a Nitroxide Radical Using 2,3-Dimethylbutadiene and 2,5-Dimethylhexadiene. Journal of the Chemical Society, Chemical Communications, 1099-1100.
14. Rockenbauer, A. and Korecz, L. (1994). Comment On The Conversion Of NO To A Nitroxide Using Butadienes. Journal of the Chemical Society, Chemical Communications, 145.
15. Morishima, I., Yoshikawa, K., Bekki, K., Kohno, M. and Arita, K. (1971). Electron Spin Resonance Spectra of Bicyclic Nitroxides. 7-Azabenzonorbornadiene-7-oxyl and 7-Azabenzonorbornene-7-oxyl. Journal of the American Chemical Society, 93, 5815-5817.
16. Alonso, T., Harvey, S., Junk, P. C., Raston, C. L., Skelton, B. W. and White, A. H. (1987). Main Group - Conjugated Organic Anon Chemistry. 1. Synthesis of Magnesium Anthracene, Silylated Anthracenes or Fluoranthene Tetrahydrofuron and Tertiary Amine Complexes and of Magnesium Cyclooctatetraene. Organometallics, 6, 2110.
17. Perkins, M. J., Ward, P. and Horsfield, A. (1970). A Probe For Homolytic Reactions In Solution. Part III Radicals By Hydrogen Abstraction. Journal of the Chemical Society B, 395-400.
18. Hudson, A. and Hussain, H. A. (1970). The Electron Spin Resonance Of Some Dialkyl Nitroxides. Journal of the Chemical Society B, 1259-1300.
19. Jantzen, E. G. (1971). The Stereochemistry Of Nitroxides. In Topics in Stereochemistry (Ed.: N.L. Allinger, E.L. Eliel), Wiley-Interscience, New York, Vol. 6, p. 177-217.
20. Yoshi, A., Yong, G. C. (1981). EPR Studies Of Nitroxides Formed In Low Temperature Photolysis Of N-Nitrosamines. Organic Magnetic Resonance, 17, 138-143.
21. Pryor, W. A., Lightsey, J. W. and Church, D. F. (1982). Reaction of Nitrogen Dioxide with Alkenes and Polyunsaturated Fatty Acids: Addition and Hydrogen Abstraction Mechanisms Journal of the American Chemical Society, 104, 6685-6692.
22. Pryor, W. A. and Lighsey, J. W. (1981). Mechanisms Of Nitrogen Dioxide Reactions: Initiation Of Lipid Peroxidation And The Production Of Nitrous Acid. Science, 214, 435-437.
23. Titov, A. I. (1963). The Free Radical Mechanism Of Nitration. Tetrahedron, 19, 557-580.
24. Marathamuthu, P. and Scaiano, J. C. (1978) Biradical Double Trapping Of NO: An EPR Study. Journal of Physical Chemistry, 82, 1588-1591.
25. Adam, W., Bottle, S. E., Grice, I. D., Pfeiler, D. and Wentrup, C. (1996). Nitric Oxide Addition To BisKetenes. Tetrahedron Letters, 37, 2113-2116.
26. Hansen, G. R. and Wang, D. (1995). A New Method For Computer Simulation Of Paramagnetic Resonance Spectra, Journal Magnetic Resonance, 117, 1-8.
27. Hansen, G. R. and Wang, D. (1996). A New Method For Simulating Powder Spectra In Magnetic Resonance. Applied Magnetic Resonance, 11, 401-415.
28. Heilbron, I. M. and Heaton, J. S. (1956). Synthesis of 9,10-Dibromoanthracene. In Organic Syntheses Collective Volume 1. (ed. H. Gilman), John Wiley & Sons, New York, second edition, 3, 41, 207-209.
29. Mikhailov, B. M. (1948). Syntheses Of Polycyclic Compounds: Lithiumorganic Compounds Of Anthracene. Izvetija Akademii Nauk S.S.S.R., 420-426.
30. Mikhailov, B. M. and Bronovilskaya, V. P. (1952). Preparation Of Derivatives Of Anthracenes With The Aid Of Lithiumorganic Compounds, Zhurnal Obsich Klüntii., 22, 157-162.
31. Meek, J. S., Monroe, P. A. and Bouboulis, C. J. (1963). Diels-Alder-Reactions of 9-Substituted Anthracenes. V Adducts of Ethylene Journal of Organic Chemistry, 28, 2572-2577.
32. Kawamura, Y., Thurnauer, M., Schuster, G. B. (1986). Putative Electrocyclic Reaction Of Cyclobutene Radical Cation: 1,2-DiPhenyl-3,3,4,4-tetramethylcyclobutene. Tetrahedron, 42, 6195-6200.
33. Horsewood, P., Kirby, G. W., Sharma, R. P., Sweeny, J. G. (1981). Formation And Thermal Cleavage Reactions Of The Cycloadduct Of 9,10-Dimethylanthracene And Nitrosyl Cyanide. Journal of the Chemical Society, Perkin 1, 6, 1802-1806.