(
4
see Fig. 4) were obtained by recording the absorption intensity at
27 nm.
6 J. Gao, J. H. Reibenspies and A. E. Martell, Inorg. Chim. Acta, 2002,
3
38, 157.
7
L. M. Mirica, M. Vance, D. J. Rudd, B. Hedman, K. O. Hodgson, E. I.
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Catalysis
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9
E. P. Zhang, H. W. Hou, H. Y. Han and Y. T. Fan, J. Organomet. Chem.,
2008, 693, 1927.
A mixture of 2,6-dimethylphenol (0.5 mmol), complex 1 (0.005
mmol) and solvent (0.5 mL) was placed in a flask. The mixture
was stirred at a certain temperature for a certain period of time
1
1
0 Y. M. Chung, W. S. Ahn and P. K. Lim, J. Mol. Catal. A: Chem., 1999,
48, 117.
1
1 (a) H. Higashimura, K. Fujisawa, Y. Moro-oka, M. Kubota, A.
Shiga, A. Terahara, H. Uyama and S. Kobayashi, J. Am. Chem. Soc.,
in the presence of O . During the reaction, the coupling product
2
1
998, 120, 8529; (b) S. Kobayashi and H. Higashimura, Prog. Polym.
precipitated out from the solution. After completion, the organic
products were separated from the reaction mixture by filtration
and the filtrate was extracted with dichloromethane (2 mL ¥
Sci., 2003, 28, 1015; (c) H. Higashimura, K. Fujisawa, M. Kubota
and S. Kobayashi, J. Polym. Sci., Part A: Polym. Chem., 2005, 43,
1
955.
2
). The extracts were combined and concentrated to give more
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1
3 S. J. A. Guieu, A. M. M. Lanfredi, C. Massera, L. D. Pach o´ n, P. Gamez
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products. All the crude products were combined, washed with
methanol (1 mL ¥ 2), and chromatographed on silica gel. Product
analysis was performed by the H NMR spectroscopic method.
The spectral data of the coupling product were essentially identical
to those reported in the literature. Other substrates were carried
out under similar reaction conditions as indicated in the table
footnotes.
1
1
1
6 M. Hirano, T. Ishii and T. Morimoto, Bull. Chem. Soc. Jpn., 1991, 64,
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1
1
7 H. Nishino, N. Itoh, M. Nagashima and K. Kurosawa, Bull. Chem.
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8 A. P. Singh and R. Gupta, Eur. J. Inorg. Chem., 2010, 4546.
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Spectral data of products
2
0 G. Pandey, C. Muralikrishna and U. T. Bhalerao, Tetrahedron Lett.,
39
1
3,5,3¢,5¢-Tetramethyldiphenoquinone.
H NMR (400 MHz,
1
990, 31, 3771.
CDCl
3
): d 7.72 (s, 4 H), 2.16 (s, 12 H). IR (KBr): 2960, 1637,
21 (a) A. Prokofieva, A. I. Prikhod’ko, S. Dechert and F. Meyer, Chem.
Commun., 2008, 1005; (b) A. Prokofieva, S. Dechert, C. Große, G. M.
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-
1
1
592, 1424 cm .
,5,3¢,5¢-Tetraisopropyldiphenoquinone. H NMR (400 MHz,
CDCl ): d 7.55 (s, 4 H), 3.01 (septet, J = 7.2 Hz, 4 H), 1.1 (d, J =
.2 Hz, 24 H). IR (KBr): 2960, 1589, 1461, 1386, 1080 cm .
17 1
3
2
3
-
1
7
40 1
3
,5,3¢,5¢-Tetra-t-butyldiphenoquinone. H NMR (400 MHz,
CDCl ): d 7.71 (s, 4 H), 1.37 (s, 36 H). IR (KBr): 2957, 1607,
457 cm .
,5,3¢,5¢-Tetramethoxydiphenoquinone. H NMR (400 MHz,
d-DMSO): d 8.2 (s, 4 H), 3.72 (s, 12 H). IR (KBr): 2988, 1662,
3
-
1
1
23 (a) S. I. Chan and S. S.-F. Yu, Acc. Chem. Res., 2008, 41, 969; (b) E. I.
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9
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1
1
557, 1441 cm .
,3¢-Di-t-butyl-5,5¢-dimethyldiphenoquinone.
400 MHz, d-acetone): d 7.66 (s, 2 H), 7.6 (s, 2 H), 2.1 (s, 6 H), 1.3
42
1
3
H
NMR
(
(
-
1
s, 18 H). IR (KBr): 2954, 1605, 1453 cm .
2
011, 50, 2133; (g) N. Fujieda, A. Yakiyama and S. Itoh, Dalton Trans.,
36 1
3
,5,3¢,5¢-Tetramethylbiphenyl-2,2¢-diol. H NMR (400 MHz,
CDCl ): d d 7.39 (d, 2 H), 7.11 (s, 2 H), 5.21 (br s, 2 H), 1.45 (s, 18
H), 1.32 (s, 18 H). IR (KBr): 3525, 2959, 1476 cm .
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3
-
1
2
43
1
Binaphthalenyl-2,2¢-diol.
H NMR (400 MHz, CDCl
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): d
7
.10–7.50 (m, 8 H), 7.80–8.00 (m, 4 H), 8.50–8.80 (br s, 2 H).
25 (a) W. L. Driessen, P. J. Baesjou, J. E. Bol, H. Kooijman, A. L. Spek
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-
1
IR (KBr): 3485, 1685, 1620, 1509, 1460 cm .
44
1
2
,5-Dimethyl-[1,4]benzoquinone.
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2
6 (a) M. Huisman, I. A. Koval, P. Gamez and J. Reedijk, Inorg. Chim.
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-
1
(
KBr): 1655, 1600 cm .
2
405.
2
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