The Reactivity of Nitrogen Dioxide with Substituted Phenols
FULL PAPER
[
4] a) J. A. I. Titov, Tetrahedron 1963, 19, 557–580; b) G. Brunton,
H. W. Cruse, K. M. Riches, A. Whittle, Tetrahedron Lett. 1979,
[24] M. H. Abraham, P. L. Grellier, D. V. Prior, P. P. Duce, J. Chem.
Soc., Perkin Trans. 2 1989, 699–711.
20, 1093–1094; c) R. J. Singh, S. P. A. Gross, J. Joseph, B. Kaly-
[25] G. Litwinienko, K. U. Ingold, J. Org. Chem. 2003, 68, 3433–
anaraman, Proc. Natl. Acad. Sci. USA 1998, 95, 12912–12917;
d) K. Kikugawa, K. Hiramoto, Y. Okamoto, Y. K. Hasegawa,
Free Radical Res. 1994, 21, 399–408; e) S. Jaffe, Chem. React.
Urban Atmos. Proc. 1971, 103–109.
3438.
[26] a) L. Valgimigli, J. T. Banks, K. U. Ingold, J. Lusztyk, J. Am.
Chem. Soc. 1995, 117, 9966–9971; b) D. V. Avila, K. U. Ingold,
J. Lusztyk, W. H. Green, D. R. Procopio, J. Am. Chem. Soc.
1
995, 117, 2929–2930; c) P. A. MacFault, K. U. Ingold, J. Lusz-
[
5] a) W. A. Pryor, J. W. Lightsey, Science 1981, 214, 435–437; b)
tyk, J. Org. Chem. 1996, 61, 1316–1321; d) L. Valgimigli, J. T.
Banks, J. Lusztyk, K. U. Ingold, J. Org. Chem. 1999, 64, 3381–
W. A. Pryor, W. Lightsey, D. F. Church, J. Am. Chem. Soc.
1
982, 104, 6685–6692; c) R. E. Huie, Toxicology 1994, 89, 193–
3
383; e) D. W. Snelgrove, J. Lusztyk, J. T. Banks, P. Mulder,
2
16; d) H. Jiang, N. Kruger, D. R. Lahiri, J.-M. Vatèle, M.
K. U. Ingold, J. Am. Chem. Soc. 2001, 123, 469–477.
Balazy, J. Biol. Chem. 1999, 274, 16235–16241.
[
[
27] a) K. U. Ingold, D. R. Taylor, Can. J. Chem. 1961, 39, 481–
[
6] a) R. E. Huie, P. Neta, J. Phys. Chem. 1986, 90, 1193–1198; b)
Z. B. Alfassi, R. E. Huie, P. Neta, J. Phys. Chem. 1986, 90,
4
87; b) G. Litwinienko, E. Megiel, M. Wojnicz, Org. Lett. 2002,
4, 2425–2428.
4
156–4158; c) Z. B. Alfassi, Int. J. Radiat. Appl. Instrum., Part
28] a) P. Franchi, M. Lucarini, G. F. Pedulli, L. Valgimigli, B. Lu-
nelli, J. Am. Chem. Soc. 1999, 121, 507–514; b) M. Lucarini,
V. Mugnaini, G. F. Pedulli, J. Org. Chem. 2002, 67, 928–931.
29] F. G. Bordwell, J.-P. Cheng, J. Am. Chem. Soc. 1991, 113, 1736–
C: Radiat. Phys. Chem. 1987, 29, 405–406.
[
7] a) W. A. Prutz, H. Monig, J. Butler, E. J. Land, Arch. Biochem.
Biophys. 1985, 243, 125–134; b) L. Batt, Int. Rev. Phys. Chem.
[
[
1
987, 6, 53–90; c) T. Logager, K. Sehested, J. Phys. Chem. 1993,
1
743.
30] Ionisation Constants of Organic Acids in Aqueous Solution
Eds.: E. P. Serjeant, B. Dempeys), IUPAC Chemical Data
Series No 23, Pergamon Press, Oxford, U.K. 1979.
9
7, 10047– 10052.
[
[
[
[
8] R. B. Coombes, A. W. Diggle, S. P. Kempsell, Tetrahedron Lett.
994, 35, 6373–6376.
9] J. J. Bozell, J. O. Hoberg, D. R. Dimmel, Tetrahedron Lett.
998, 39, 2261–2264.
(
1
[31] a) G. Litwinienko, K. U. Ingold, J. Org. Chem. 2003, 68, 3433–
1
3438; b) M. C. Foti, C. Daquino, C. Geraci, J. Org. Chem.
2
004, 69, 2309–2314; c) G. Litwinienko, K. U. Ingold, J. Org.
10] W. H. Koppenol, J. J. Moreno, W. A. Pryor, H. Hischiropoulos,
J. S. Beckman, Chem. Res. Toxicol. 1992, 5, 834–842.
Chem. 2004, 69, 5888–5896.
[
32] a) B. C. Challis, D. E. Shuker, D. H. Fine, E. U. Goff, G. A.
Hoffman, IARC Sci. Publ. 1982, 11–20; b) W. A. Pryor, D. F.
Church, C. K. Govidan, G. Crank, J. Org. Chem. 1982, 47,
11] M. H. Abraham, P. L. Grellier, D. V. Prior, P. P. Duce, J. J.
Morris, P. J. Taylor, J. Chem. Soc., Perkin Trans. 2 1990, 521–
5
29.
12] a) C. H. Bibart, G. E. Ewing, J. Chem. Phys. 1974, 61, 1284–
292; b) B. W. McLelland, G. Gunderson, K. Hudberg, J.
156–159.
[
[
[
33] L. Parts, J. T. Miller Jr., J. Chem. Phys. 1965, 43, 136–139.
1
34] K. Y. Lee, D. J. Kuchynka, J. K. Kochi, Inorg. Chem. 1990, 29,
Chem. Phys. 1972, 56, 4541–4545.
4196–4204.
[
[
[
13] R. B. Coombes, A. W. Diggle, S. P. Kempsell, Tetrahedron Lett.
[35] M. R. Gunther, L. C. Hsi, J. F. Curtis, L. J. Marnett, T. E.
Eling, R. P. Mason, J. Biol. Chem. 1997, 272, 17086–17090.
[36] A. J. Parker, Quart. Rev. 1962, 16, 163–187.
[37] K. Takaki, Y. Shimasaki, T. Shishido, K. Takehira, Bull. Chem.
Soc. Jpn. 2002, 75, 311–317.
[38] H. Weiner, R. Finke, J. Am. Chem. Soc. 1999, 121, 9831–9842.
[39] J.-M. Poirier, C. Vottero, Tetrahedron 1989, 45, 1415–1422.
[40] J. Rojo, J.-M. Lehn, G. Baum, D. Fenske, O. Waldmann, P.
Müller, Eur. J. Inorg. Chem. 1999, 517–522.
1
993, 34, 8557–8560.
14] A. Fischer, N. Mathivanan, Tetrahedron Lett. 1988, 29, 1869–
872.
1
15] M. R. Amin, L. Dekker, D. B. Hibbert, J. H. Ridd, J. P. B. San-
dall, J. Chem. Soc., Chem. Commun. 1986, 658–659.
[
[
16] M. P. Hartshorn, Acta Chem. Scand. 1998, 52, 2–10.
17] a) M. P. Harshorn, W. T. Robinson, J. Vaughan, J. M. White,
Aust. J. Chem. 1985, 38, 145–160; b) M. P. Hartshorn, R. J.
Martyn, W. T. Robbinson, K. H. Sutton, J. Vaughan, J. M.
White, Aust. J. Chem. 1985, 38, 1613–1690.
[41] M. P. Hartshorn, W. T. Robinson, K. H. Sutton, J. Vaugham,
Aust. J. Chem. 1985, 38, 161–177.
[
18] a) P. G. Ashmore, B. J. Tyler, J. Chem. Soc. 1961, 1017–1021;
[42] A. F. Hegarty, J. P. Keogh, J. Chem. Soc., Perkin Trans. 2 2001,
b) P. L. Asquith, B. J. Tyler, J. Chem. Soc., Chem. Commun.
758–762.
1
970, 744–745.
[43] M. P. Hartshorn, K. H. Sutton, J. Vaugham, Aust. J. Chem.
1983, 36, 2339–2348.
[44] S. Futamura, K. Yamazaki, H. Ohta, Y. Kamiya, Bull. Chem.
Soc. Jpn. 1982, 55, 3852–3855.
[45] C. D. Selassie, R. P. Verma, S. Kapur, A. J. Shusterman, C.
Hansch, J. Chem. Soc., Perkin Trans. 2 2002, 1112–1117.
[46] K. Omura, Synthesis 1998, 1145–1148.
[47] H. W. Heine, J. C. Ciaccio, K. G. Carson, C. M. Taylor, J. Org.
Chem. 1990, 55, 4039–4043.
[
[
[
[
19] W. A. Prutz, H. Monig, J. Butler, E. J. Land, Arch. Biochem.
Biophys. 1985, 243, 125–134.
20] E. P. L. Hunter, M. F. Desrosiers, M. G. Simic, Free Radical
Biol. Med. 1989, 6, 581585.
21] G. G. Cross, A. Fischer, G. N. Henderson, Can. J. Chem. 1984,
6
2, 2803–2812.
22] The BDE value was calculated from the formation enthalpies
of the compounds and the radicals obtained from their dissoci-
ation: J. Phys. Chem. Ref. Data 1985, Vol. 14.
[48] S. D. Bohle, J. A. Imonigie, J. Org. Chem. 2000, 65, 5685–5692.
[49] Y. Kotake, E. Janzen, Can. J. Chem. 1988, 66, 1895–1900.
Received: January 10, 2005
[
23] E. T. Denisov, in Handbook of Antioxidants, CRC Press, Inc.,
Boca Raton 1995.
Eur. J. Org. Chem. 2005, 3052–3059
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