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0003829752
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John Wiley & Sons: Chichester
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Patai, S.; Rappoport, Z. The Chemistry of the Quinonoid Compounds; John Wiley & Sons: Chichester, 1988; Vol 2, Part 1 and Part 2; Thomson, R. H. Naturally Occurring Quinones IV Recent Advances; Blackie Academic & Professional; London, 1997; Gallagher, P. T. Contemp. Org. Synth. 1996, 3, 433.
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The Chemistry of the Quinonoid Compounds
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Patai, S.1
Rappoport, Z.2
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2
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0003868021
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Blackie Academic & Professional; London
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Patai, S.; Rappoport, Z. The Chemistry of the Quinonoid Compounds; John Wiley & Sons: Chichester, 1988; Vol 2, Part 1 and Part 2; Thomson, R. H. Naturally Occurring Quinones IV Recent Advances; Blackie Academic & Professional; London, 1997; Gallagher, P. T. Contemp. Org. Synth. 1996, 3, 433.
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Naturally Occurring Quinones IV Recent Advances
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Thomson, R.H.1
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3
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0001351957
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Patai, S.; Rappoport, Z. The Chemistry of the Quinonoid Compounds; John Wiley & Sons: Chichester, 1988; Vol 2, Part 1 and Part 2; Thomson, R. H. Naturally Occurring Quinones IV Recent Advances; Blackie Academic & Professional; London, 1997; Gallagher, P. T. Contemp. Org. Synth. 1996, 3, 433.
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Contemp. Org. Synth.
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7
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84989432831
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Syper, L.; Kloc, K.; Mlochowski, J.; Szulc, Z. Synthesis, 1979, 521; Syper, L.; Kloc, K.; Mlochowski, J. Tetrahedron 1980, 36, 123.
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Synthesis
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Syper, L.1
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8
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46749095665
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Syper, L.; Kloc, K.; Mlochowski, J.; Szulc, Z. Synthesis, 1979, 521; Syper, L.; Kloc, K.; Mlochowski, J. Tetrahedron 1980, 36, 123.
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Tanoue, Y.; Sakata, K.; Hashimoto, M.; Morishita, S.; Hamada, M.; Kai, N.; Nagai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2593.
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Kai, N.6
Nagai, T.7
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12
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0001116597
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3 has previously been used for oxidative couplings to biaryls (in trifluoroacetic acid, reflux), see: McKillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504; Debad, J. D.; Morris, J. C.; Lynch, V.; Magnus, P.; Bard, A. J. J. Am. Chem. Soc. 1996, 118, 2374; Debad, J. D.; Morris, J. C.; Magnus, P.; Bard, A. J. J. Org. Chem. 1997, 62, 530.
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13
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0029971353
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3 has previously been used for oxidative couplings to biaryls (in trifluoroacetic acid, reflux), see: McKillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504; Debad, J. D.; Morris, J. C.; Lynch, V.; Magnus, P.; Bard, A. J. J. Am. Chem. Soc. 1996, 118, 2374; Debad, J. D.; Morris, J. C.; Magnus, P.; Bard, A. J. J. Org. Chem. 1997, 62, 530.
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Debad, J.D.1
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Magnus, P.4
Bard, A.J.5
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14
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0002022792
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3 has previously been used for oxidative couplings to biaryls (in trifluoroacetic acid, reflux), see: McKillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504; Debad, J. D.; Morris, J. C.; Lynch, V.; Magnus, P.; Bard, A. J. J. Am. Chem. Soc. 1996, 118, 2374; Debad, J. D.; Morris, J. C.; Magnus, P.; Bard, A. J. J. Org. Chem. 1997, 62, 530.
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J. Org. Chem.
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Debad, J.D.1
Morris, J.C.2
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Bard, A.J.4
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15
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0003998388
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CRC Press: Boca Raton, Florida, standard reduction potentials are as follows: Ag(II) + e = Ag(I), 1.98 V; Co(III) + e = Co(II), 1.92 V; Ce(IV) + e = Ce(III), 1.72 V
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According to CRC Handbook of Chemistry and Physics (79th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, Florida, 1998-1999; p 8-21), standard reduction potentials are as follows: Ag(II) + e = Ag(I), 1.98 V; Co(III) + e = Co(II), 1.92 V; Ce(IV) + e = Ce(III), 1.72 V.
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(1998)
CRC Handbook of Chemistry and Physics 79th Ed.
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Lide, D.R.1
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16
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85069277169
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note
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2O, pyridine, rt, 1 d.
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17
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85069282904
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note
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3 (Aldrich) in a glove bag under an argon atmosphere.
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18
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85069284229
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note
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Besides dioxane and acetonitrile, nitromethane could also be used as the solvent. Acetone and t-BuOH could also be used although longer reaction times were required.
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19
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85069281778
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note
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The obtained quinones were characterized by analytical data (NMR, IR, and MS spectra and mp). The known quinones are as follows: 4a (= 2), commercially available; 4b, commercially available; 4c, see ref 19; 4d, see ref 27; 6a, commercially available; 6b, see ref 20, 28; 6c, see ref 29; 6d, see ref 30; quinone derived from 7, see ref 6.
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20
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Staab, H. A.; Herz, C. P.; Henke, H.-E. Chem. Ber. 1977, 110, 3351; Nicoletti, T. M.; Raston, C. L., Sargent, M. V. J. Chem. Soc., Perkin Trans. I, 1990, 133.
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Staab, H. A.; Herz, C. P.; Henke, H.-E. Chem. Ber. 1977, 110, 3351; Nicoletti, T. M.; Raston, C. L., Sargent, M. V. J. Chem. Soc., Perkin Trans. I, 1990, 133.
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25
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0011741104
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Tanoue, Y.; Terada, A.; Matsumoto, Y. Bull. Chem. Soc. Jpn. 1989, 62, 2736; Syper, L. Synthesis, 1989, 167.
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Tanoue, Y.; Terada, A.; Matsumoto, Y. Bull. Chem. Soc. Jpn. 1989, 62, 2736; Syper, L. Synthesis, 1989, 167.
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Syper, L.1
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27
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85069278994
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Jpn. Kokai Tokkyo Koho JP 11 21262 [99 21262]
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Satomi, T.; Takeda, M.; Tanaka, M. Jpn. Kokai Tokkyo Koho JP 11 21262 [99 21262]; Chem. Abstr. 1999, 130, 178750.
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