The Journal of Organic Chemistry
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V. D.; Ronlan, A. J. Am. Chem. Soc. 1976, 98, 2571. (b) Reference 9j.
(c) Reference 9l.
(16) Literature references for the oxidation potential of 1,4-
dimethoxybenzene: (a) Reference 9b. (b) Reference 9e. (c)
Reference 9f. (d) Reference 9g. (e) Reference 11f. (f) Onodera, K.;
Furusawa, G.-I.; Kojima, M.; Tsuchiya, M.; Aihara, S.; Akaba, R.;
Sakuragi, H.; Tokumaru, K. Tetrahedron 1985, 41, 2215. (g) Anelli, P.
L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M.
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193. (h) Reference 10b. (i) Reference 9h. (j) Benniston, A. C.;
Harriman, A.; Lynch, V. M. J. Am. Chem. Soc. 1995, 117, 5275.
(k) Rehm, J. M.; McLendon, G. L.; Fauchet, P. M. J. Am. Chem. Soc.
1996, 118, 4490. (l) Ballardini, R.; Balzani, V.; Credi, A.; Brown, C. L.;
Gillard, R. E.; Montalti, M.; Philp, D.; Stoddart, J. F.; Venturi, M.;
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V.; Parfenov, N. N.; Petrosyan, V. A. Russ. Chem. Bull. 2002, 51, 998.
(n) Reference 13e. (o) Reference 10d. (p) Shukla, D.; Liu, G.;
Dinnocenzo, J. P.; Farid, S. Can. J. Chem. 2003, 81, 744. (q) Svith, H.;
(4) For reviews of the redox equilibrium method applied in water and
alcoholic solvents, see: (a) Steenken, S. Landolt-Bornstein 1985, 13e,
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147. (b) Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637.
(c) Stanbury, D. M. In General Aspects of the Chemistry of Radicals;
Alfassi, Z. B., Ed.; Wiley: New York, 1999; Chapter 11.
(5) The standard deviation in the last significant digit is given in
parentheses.
(6) Amatore, C.; Lefrou, C. J. Electroanal. Chem. 1992, 325, 239.
(7) Literature oxidation potentials in acetonitrile not referenced to
SCE were corrected according to ref 7a: (a) Mann, C. K.; Barnes, K. K.
Electrochemical Reactions in Nonaqueous Systems; Marcel Dekker: New
York, 1970; p 26. For the Ag/AgI reference electrode, the correction to
SCE was applied according to ref 7b: (b) Rondinini, S.; Longhi, P.;
Mussini, T. Ann. Chim. (Rome, Italy) 1977, 67, 48.
(8) Literature references for the oxidation potential of diphenyl ether:
(a) Janissek, P. R.; Pardini, V. L.; Viertler, H. J. Chem. Soc., Chem.
Commun. 1987, 576. (b) Yamada, F.; Nishiyama, T.; Nakai, Y.; Nishii,
S. Technol. Rep. Kansai Univ. 1988, 30, 91.
Jensen, H.; Almstedt, J.; Andersson, P.; Lundback, T.; Daasbjerg, K.;
̈
Jonsson, M. J. Phys. Chem. A 2004, 108, 4805. (r) Zeng, C.-C.; Becker,
J. Y. J. Org. Chem. 2004, 69, 1053. (s) Reference 10e. (t) Reference 9j.
(u) Yuasa, J.; Fukuzumi, S. Chem. Commun. 2006, 561. (v) Sunahara,
H.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129,
5597. (w) Reference 10g.
(17) Literature references for the oxidation potential of 1,2,3,5-
tetramethoxybenzene: (a) Reference 9b. (b) Reference 11g.
(18) Literature references for the oxidation potential of 1,2,4-
trimethoxybenzene: (a) Reference 9b. (b) Reference 16k. (c)
Reference 10e. (d) Reference 16u. (e) Reference 9j. (f) Reference 9l.
(19) Literature references for the oxidation potential of indole:
(a) Waltman, R. J.; Diaz, A. F.; Bargon, J. J. Phys. Chem. 1984, 88, 4343.
(b) Giessler, A.; Steckhan, E.; Wiest, O.; Knoch, F. J. Org. Chem. 1991,
56, 1405. (c) Newman, J. D. S.; Blanchard, G. J. Langmuir 2006, 22,
5882. (d) Huvaere, K.; Skibsted, L. H. J. Am. Chem. Soc. 2009, 131,
8049. (e) Yin, B.; Wang, L.; Inagi, S.; Fuchigami, T. Tetrahedron 2010,
66, 6820.
(9) Literature references for the oxidation potential of anisole:
(a) Lund, H. Acta Chem. Scand. 1957, 11, 1323. (b) Zweig, A.;
Hodgson, W. G.; Jura, W. H. J. Am. Chem. Soc. 1964, 86, 4124.
(c) Miller, L. L.; Nordblom, G. D.; Mayeda, E. A. J. Org. Chem. 1972,
37, 916. (d) Perrin, C. L. J. Am. Chem. Soc. 1977, 99, 5516. (e) Birch, A.
J.; Slobbe, J. Aust. J. Chem. 1978, 31, 2555. (f) Majima, T.; Pac, C.;
Nakasone, A.; Sakurai, H. J. Am. Chem. Soc. 1981, 103, 4499.
(g) Kawenoki, I.; Keita, B.; Kossanyi, J.; Nadjo, L. Bull. Soc. Chim. Fr.
1982, 104. (h) Burget, D.; Jacques, P.; Vauthey, E.; Suppan, P.;
Haselbach, E. J. Chem. Soc., Faraday Trans. 1994, 90, 2481. (i) van
Walree, C. A.; Roest, M. R.; Schuddeboom, W.; Jenneskens, L. W.;
Verhoeven, J. W.; Warman, J. M.; Kooijman, H.; Spek, A. L. J. Am.
Chem. Soc. 1996, 118, 8395. (j) Branchi, B.; Galli, C.; Gentili, P. Org.
Biomol. Chem. 2005, 3, 2604. (k) Tajima, T.; Nakajima, A. J. Am. Chem.
Soc. 2008, 130, 10496. (l) Ohkubo, K.; Mizushima, K.; Iwata, R.;
Fukuzumi, S. Chem. Sci. 2011, 2, 715.
(20) Literature references for the oxidation potential of N-
methylindole: (a) Reference 19a. (b) Pozkarskii, A. F.; Kuz’menko,
́
(10) Literature references for the oxidation potential of 1,3-
dimethoxybenzene: (a) Reference 9e. (b) Suzuki, T.; Fujii, H.;
Yamashita, Y.; Kabuto, C.; Tanaka, S.; Harasawa, M.; Mukai, T.;
Miyashi, T. J. Am. Chem. Soc. 1992, 114, 3034. (c) Patz, M.; Mayr, H.;
Maruta, J.; Fukuzumi, S. Angew. Chem. 1995, 107, 1351. (d) Tomma-
V. V.; Bumber, A. A.; Petrov, E. S.; Terekhova, M. I.; Chikina, N. L.;
Nanavyan, I. M. Chem. Heterocycl. Compd. 1989, 25, 180. (c) Reference
19b. (d) Berlin, A.; Canavesi, A.; Schiavon, G.; Zecchin, S.; Zotti, G.
Tetrahedron 1996, 52, 7947. (e) Reference 19d.
(21) Literature references for the oxidation potential of 4-cyano-N,N-
dimethylaniline: (a) Macdonald, T. L.; Gutheim, W. G.; Martin, R. B.;
Guengerich, F. P. Biochemistry 1989, 28, 2071. (b) Fukuzumi, S.;
Shimoosako, K.; Suenobu, T.; Watanabe, Y. J. Am. Chem. Soc. 2003,
125, 9074. (c) Baciocchi, E.; Bietti, M.; Gerini, M. F.; Lanzalunga, O. J.
Org. Chem. 2005, 70, 5144.
(22) Literature reference for the oxidation potential of 4-
trifluoromethyl-N,N-dimethylaniline: Dombrowski, G. W.;
Dinnocenzo, J. P.; Zielinski, P. A.; Farid, S.; Wosinska, Z. M.; Gould,
I. R. J. Org. Chem. 2005, 70, 3791.
(23) Literature references for the oxidation potential of 2-
methylindole: (a) Alberti, A.; Carloni, P.; Eberson, L.; Greci, L.;
Stipa, P. J. Chem. Soc., Perkin Trans. 2 1997, 887. (b) Reference 19a.
(c) Reference 20d.
́
sino, J.-B.; Brondex, A.; Medebielle, M.; Thomalla, M.; Langlois, B. R.;
Billard, T. Synlett 2002, 1697. (e) Fukuzumi, S.; Yuasa, J.; Satoh, N.;
Suenobu, T. J. Am. Chem. Soc. 2004, 126, 7585. (f) Reference 9l.
(g) Breton, G. W.; Hoke, K. R. J. Org. Chem. 2013, 78, 4697.
(11) Literature references for the oxidation potential of 1,3,5-
trimethoxybenzene: (a) Reference 9b. (b) Reference 9g. (c) Mizuno,
K.; Yoshioka, K.; Otsuji, Y. Chem. Lett. 1983, 941. (d) Reference 10c.
(e) Reference 9f. (f) Pouliquen, J.; Wintgens, V.; Toscano, V.; Jaafar, B.
B.; Tripathi, S.; Kossanyi, J.; Valat, P. Can. J. Chem. 1984, 62, 2478.
(g) Wolfle, I.; Lodaya, J.; Sauerwein, B.; Schuster, G. B. J. Am. Chem.
Soc. 1992, 114, 9304. (h) Dileesh, S.; Gopidas, K. R. J. Photochem.
Photobiol., A 2004, 162, 115. (i) Reference 9l. (j) Reference 10g.
(12) Literature references for the oxidation potential of 1,3-
benzodioxole: (a) Yan, B.-Z.; Zhang, Z.-G.; Yuan, H.-C.; Wang, L.-
C.; Xu, J.-H. J. Chem. Soc., Perkin Trans. 2 1994, 2545. (b) Rudenko, A.
P.; Pragst, F. Russ. J. Org. Chem. 1998, 34, 1589.
(24) Literature references for the oxidation potential of 3-
methylindole: (a) Reference 19a. (b) Reference 20d. (c) Reference
19d. (d) Reference 19e.
(13) Literature references for the oxidation potential of 1,2-
dimethoxybenzene: (a) Reference 9b. (b) Reference 9f. (c) Reference
11f. (d) Reference 10b. (e) Deffieux, D.; Fabre, I.; Courseille, C.;
Quideau, S. J. Org. Chem. 2002, 67, 4458. (f) Reference 10e. (g)
Reference 9j. (h) Reference 9k. (i) Reference 9l.
(14) Literature references for the oxidation potential of 1,2,3-
trimethoxybenzene: (a) Reference 9b. (b) Reference 9l.
(15) Literature references for the oxidation potential of 1,2-
dimethoxy-4-methylbenzene: (a) Palmquist, U.; Nilsson, A.; Parker,
(25) Literature reference for the oxidation potential of 4-
methylcarboxy-N,N-dimethylaniline: Renaud, R. N.; Stephens, C. J.;
Brochu, G. Can. J. Chem. 1984, 62, 565.
(26) Literature references for the oxidation potential of aniline: (a)
́ ́
Reference 9a. (b) Parkanyi, C.; Zahradník, R. Collect. Czech. Chem.
Commun. 1965, 30, 4287. (c) Lutskii, A. E.; Beilis, Yu. I.; Fedorchenko,
V. I. Zh. Obshch. Khim. 1972, 42, 2535. (d) Jones, P. R.; Drews, M. J.;
Johnson, J. K.; Wong, P. S. J. Am. Chem. Soc. 1972, 94, 4595. (e) Sasaki,
K.; Kitani, A.; Tsuboi, M. Nippon Kagaku Kaishi 1973, 2269. (f) Hand,
9303
dx.doi.org/10.1021/jo501761c | J. Org. Chem. 2014, 79, 9297−9304