Mechanistic studies on the free radical decomposition of some oxalic acid arylhydrazides: A source of aryl radicals in aqueous solution

Arkivoc

Volumn 2006, Issue 3, 2005, Pages 127-147

  Gilbert, Bruce C ^a   Ionita, Petre ^a   Lindsay Smith, John R ^a   Oakes, John ^b   Ouwerkerk, Niels ^c  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

^c UNILEVER RESEARCH VLAARDINGEN   (Netherlands)

Author keywords

Aryl radicals; di (arylhydrazides); Dioxygen; Mono arylhydrazides; Oxidation

Indexed keywords

EID: 27744531011     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (55)

1. Toth, B. Cancer Res., 1975, 35, 3693.
2. Spearman, M. E.; Franck, T. G.; Moloney, S. J.; Prough, R. A. In Biological oxidation of nitrogen in Organic molecules; Gorrod, J. W.; Damani, L. A. Eds.; Ellis Horwood, 1985, Ch. 11.
3. (a) Chattaway, F. D. J. Chem. Soc. 1907, 1323
4. Chattaway, F. D. and J. Chem. Soc. 1908, 270.
5. (b) Smith, P. A. S. In Openchain nitrogen compounds; Benjamin, 1966, Vol. 2, Ch. 9.
6. (c) Misra, H. P.; Fridovich, I. Biochemistry 1976, 15, 681.
7. Nelson, S. D.; Mitchell, J. R.; Timbrell, J. A.; Snodgrass, W. R.; Corcoran, G. B. Science 1976, 193, 901.
8. Moloney, S. J.; Prough, R. A. Rev. Biochem. Toxicol. 1983, 5, 313.
9. Moloney, S. J.; Wiebkin, P.; Cummings, S. W.; Prough, R. A. Carcinogenesis 1985, 6, 397.
10. Hidaka, H.; Udenfriend, S. Arch. Biochem Biophys. 1970, 140, 174.
11. Allison, W. C.; Swain, L. C.; Tracy, S. M.; Benitez, L. V. Arch. Bichem. Biophys. 1973, 155, 400.
12. Allison, W.C.; Swain, L. C. Arch. Bichem. Biophys. 1973, 155, 405.
13. Patek, D. R.; Hellerman, L. J. Biol. Chem. 1974, 249, 2373.
14. (a) Lamberg, R.; Legge, J. M. In Hematin compounds and bile pigments, Interscience, 1949, p 392.
15. (b) Beavan, G. H.; White, J. C. Nature 1954, 173, 389.
16. (c) Warburg, O.; Kubowitz, B. A.; Peisach, J.; Blumberg, W. E. Proc. Natl. Acad. Sci. USA 1970, 67, 1846.
17. Jain, K. J.; Hochstein, P. Biochim. Biophys. Acta 1979, 586, 128.
18. (a) Hill, H. A. O.; Thornalley, P. J. FEBS Letters 1981, 125, 235.
19. (b) Hill, H. A. O.; Thornalley, P. J. Can. J. Chem. 1982, 60, 1528.
20. (a) Ator, M. A.; Ortiz de Montellano, P. R. J. Biol. Chem. 1987, 262, 1542.
21. (b) Gilfoyle, D. J.; Rodriguez-Lopez, J. N.; Smith, A. T. Eur. J. Biochem. 1996, 236, 714.
22. (a) Ringe, D.; Petsko, G. A.; Kerr, D. E.; Ortiz de Montellano, P. R. Biochem. 1984, 23, 2.
23. (b) Swanson, B. A.; Ortiz de Montellano, P. R. J. Am. Chem. Soc., 1991, 113, 8146.
24. Ortiz de Montellano, P. R.; Kerr, D. E. J. Biol. Chem. 1983, 258, 10558.
25. (a) Jonen, H. G.; Werringloer, J.; Prough, R. A.; Estabrook, R. W. J. Biol. Chem. 1982, 257, 4404.
26. (b) Swanson, B. A.; Halpert, J. R.; Bornheim, L. M.; Ortiz de Montellano, P. R. Arch. Biochem. Biophys. 1992, 292, 42.
27. Samokyszyn, V. M.; Ortiz de Montellano, P. R. Biochem. 1991, 30, 11646.
28. Ortiz de Montellano, P. R. Ann. Rev. Pharmacol. Toxicol. 1992, 32, 89.
29. (a) Shinohara, K.-I.; Bayer, E. J. Photographic Sci. 1987, 35, 181;
30. (b) Chen, P.; Sun, R.-D.; Zheng, D.-S. J. Photographic Sci. 1992, 40, 118;
31. (c) Chen, P.; Sun, R.-D.; Li, X.-H.; Zheng, D.-S. J. Imaging Sci. Technol. 1993, 37, 281;
32. (d) Bowman, W. R.; Forshaw, J. A.; Hall, K. P.; Kitchin, J. P.; Mott, A. W. Tetrahedron 1996, 52, 3961.
33. Stauffer, R. E.; Smith, W. F.; Trivelli, A. P. H. J. Franklin Inst. 1944, 238, 291.
34. (a) Kitchin, J. P.; Hall, K. P.; Mott, A. W.; Marchesano, C.; Bowman, W. R. J. Photographic Sci. 1987, 35, 162.
35. (b) Pladziewicz, J. R.; Slattum, P.; Sahyun, M. R. V. J. Imaging Sci. 1989, 33, 119.
36. (c) Kitchin, J. P.; Hall, K. P.; Mott, A.W.; Marchesano, C.; Bowman, W. R. J. Imaging Technol. 1989, 15, 282.
37. (d) Halland, K. P.; Mott, A. W. US Patent 4,798,780, 1989.
38. (e) Chen, S.-L.; Ji, S.-X.; Zhu, Z.-H.; Yao, Z.-G. Dyes and Pigments 1994, 25, 101.
39. Buettner, G. R. Free Rad. Bio. Med. 1987, 3, 259.
40. Johnstone, R. A. W.; Neville, A. F.; Russell, P. J. J. Chem. Soc. B 1971, 1183.
41. th Edn.; 2003, p 8.
42. Smith, P. A. S. In Derivatives of hydrazine and other hydronitrogens having N-N bonds, Benjamin/Cummings, 1983; p 3.
43. Cohen, S. G.; Nicholson, J. J. Org. Chem. 1965, 31, 1162.
44. (a) Bunnett, J. F.; Happer, D. A. R. J. Org. Chem. 1966, 31, 2369.
45. (b) Bunnett, J. F.; Takayama, H. J. Am. Chem. Soc. 1968, 90, 5173.
46. Kosower, E. M., Acc. Chem. Res. 1971, 3, 193.
47. Smith, P. A. S. In Open-chain nitrogen compounds, Benjamin, 1966, Vol. 2, p 345.
48. Boelsing, T., Chem. Ber. 1892, 25, 1554.
49. (a) McBride, W. R.; Bens, E. M., J. Am. Chem. Soc. 1959, 81, 5546.
50. (b) Abramovitch, R. A.; Davis, B. A., Chem. Rev. 1964, 64, 149.
51. (b) Bhatnagar, I.; George, M. V. J. Org. Chem. 1968, 33, 2407.
52. Nothnagle, R. J. US Patent, 4,269,929 1980.
53. (a) Cohen, G.; Hochstein, P. Biochemistry 1964, 3, 389.
54. (b) Cohen, G.; Hochstein, P. J. Pharmacol. Exp. Ther. 1965, 147, 139.
55. Huang, P. C.; Kosower, E. M. J. Am. Chem. Soc. 1968, 90, 2354