메뉴 건너뛰기




Volumn , Issue 9, 1999, Pages 1474-1476

Synthesis of quinones from hydroquinone dimethyl ethers. Oxidative demethylation with cobalt(III) fluoride

Author keywords

Cobalt(III) fluoride; Hydroquinone dimethyl ethers; Oxidative demethylation; Quinones; Reduction potential

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; BENZOQUINONE DERIVATIVE; COBALT; FLUORIDE; HYDROQUINONE DERIVATIVE; QUINONE DERIVATIVE;

EID: 0032875336     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2875     Document Type: Article
Times cited : (23)

References (46)
  • 1
    • 0003829752 scopus 로고
    • John Wiley & Sons: Chichester
    • 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.
    • (1988) The Chemistry of the Quinonoid Compounds , vol.2 , Issue.PART 1 AND PART 2
    • Patai, S.1    Rappoport, Z.2
  • 2
    • 0003868021 scopus 로고    scopus 로고
    • Blackie Academic & Professional; London
    • 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.
    • (1997) Naturally Occurring Quinones IV Recent Advances
    • Thomson, R.H.1
  • 3
    • 0001351957 scopus 로고    scopus 로고
    • 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.
    • (1996) Contemp. Org. Synth. , vol.3 , pp. 433
    • Gallagher, P.T.1
  • 8
    • 46749095665 scopus 로고
    • Syper, L.; Kloc, K.; Mlochowski, J.; Szulc, Z. Synthesis, 1979, 521; Syper, L.; Kloc, K.; Mlochowski, J. Tetrahedron 1980, 36, 123.
    • (1980) Tetrahedron , vol.36 , pp. 123
    • Syper, L.1    Kloc, K.2    Mlochowski, J.3
  • 12
    • 0001116597 scopus 로고
    • 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.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6504
    • McKillop, A.1    Turrell, A.G.2    Young, D.W.3    Taylor, E.C.4
  • 13
    • 0029971353 scopus 로고    scopus 로고
    • 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.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2374
    • Debad, J.D.1    Morris, J.C.2    Lynch, V.3    Magnus, P.4    Bard, A.J.5
  • 14
    • 0002022792 scopus 로고    scopus 로고
    • 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.
    • (1997) J. Org. Chem. , vol.62 , pp. 530
    • Debad, J.D.1    Morris, J.C.2    Magnus, P.3    Bard, A.J.4
  • 15
    • 0003998388 scopus 로고    scopus 로고
    • 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
    • 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.
    • (1998) CRC Handbook of Chemistry and Physics 79th Ed. , pp. 8-21
    • Lide, D.R.1
  • 16
    • 85069277169 scopus 로고    scopus 로고
    • note
    • 2O, pyridine, rt, 1 d.
  • 17
    • 85069282904 scopus 로고    scopus 로고
    • note
    • 3 (Aldrich) in a glove bag under an argon atmosphere.
  • 18
    • 85069284229 scopus 로고    scopus 로고
    • note
    • 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.
  • 19
    • 85069281778 scopus 로고    scopus 로고
    • note
    • 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.
  • 22
    • 37049171812 scopus 로고
    • Fisher, G. H.; Moreno, H. R.; Oatis, J. E., Jr.; Schultz, H. P. J. Med. Chem. 1975, 18, 746; Rubenstein, L. J. Chem. Soc. 1925, 1998.
    • (1925) J. Chem. Soc. , pp. 1998
    • Rubenstein, L.1
  • 23
    • 84982063447 scopus 로고
    • 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.
    • (1977) Chem. Ber. , vol.110 , pp. 3351
    • Staab, H.A.1    Herz, C.P.2    Henke, H.-E.3
  • 26
    • 85083230568 scopus 로고
    • Tanoue, Y.; Terada, A.; Matsumoto, Y. Bull. Chem. Soc. Jpn. 1989, 62, 2736; Syper, L. Synthesis, 1989, 167.
    • (1989) Synthesis , pp. 167
    • Syper, L.1
  • 27
    • 85069278994 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho JP 11 21262 [99 21262]
    • Satomi, T.; Takeda, M.; Tanaka, M. Jpn. Kokai Tokkyo Koho JP 11 21262 [99 21262]; Chem. Abstr. 1999, 130, 178750.
    • Satomi, T.1    Takeda, M.2    Tanaka, M.3
  • 28
    • 85069283497 scopus 로고    scopus 로고
    • Satomi, T.; Takeda, M.; Tanaka, M. Jpn. Kokai Tokkyo Koho JP 11 21262 [99 21262]; Chem. Abstr. 1999, 130, 178750.
    • (1999) Chem. Abstr. , vol.130 , pp. 178750
  • 30
    • 85069276936 scopus 로고
    • Nakao, H.; Fukushima, M.; Torizuka, T. Sankyo Kenkyusho Nempo 1970, 22, 90; Chem Abstr. 1971, 75, 5400.
    • (1971) Chem Abstr. , vol.75 , pp. 5400
  • 34
    • 85069276176 scopus 로고    scopus 로고
    • Japan Kokai 74 130721
    • Kitamura, M.; Ito, T.; Sasaki, N. Japan Kokai 74 130721; Chem. Abstr. 1975, 83, 18986; Takahashi, H,; Nishi, K. Japan Kokai 76 68629; Chem. Abstr. 1977, 86, 56731.
    • Kitamura, M.1    Ito, T.2    Sasaki, N.3
  • 35
    • 85069282812 scopus 로고
    • Kitamura, M.; Ito, T.; Sasaki, N. Japan Kokai 74 130721; Chem. Abstr. 1975, 83, 18986; Takahashi, H,; Nishi, K. Japan Kokai 76 68629; Chem. Abstr. 1977, 86, 56731.
    • (1975) Chem. Abstr. , vol.83 , pp. 18986
  • 36
    • 85069276991 scopus 로고    scopus 로고
    • Japan Kokai 76 68629
    • Kitamura, M.; Ito, T.; Sasaki, N. Japan Kokai 74 130721; Chem. Abstr. 1975, 83, 18986; Takahashi, H,; Nishi, K. Japan Kokai 76 68629; Chem. Abstr. 1977, 86, 56731.
    • Takahashi, H.1    Nishi, K.2
  • 37
    • 85069275913 scopus 로고
    • Kitamura, M.; Ito, T.; Sasaki, N. Japan Kokai 74 130721; Chem. Abstr. 1975, 83, 18986; Takahashi, H,; Nishi, K. Japan Kokai 76 68629; Chem. Abstr. 1977, 86, 56731.
    • (1977) Chem. Abstr. , vol.86 , pp. 56731
  • 38
    • 0009683797 scopus 로고
    • Rabjohn, N. Ed.; John Wiley & Sons: New York, Collec.
    • Gunstone, F. D.; Tucker, S. H. In Org. Synth.; Rabjohn, N. Ed.; John Wiley & Sons: New York, 1963; Collec. Vol. 4, p 160.
    • (1963) Org. Synth. , vol.4 , pp. 160
    • Gunstone, F.D.1    Tucker, S.H.2
  • 43
    • 0344596007 scopus 로고
    • Andrews, K. J. M.; Marrian, D. H.; Maxwell, D. R. J. Chem. Soc. 1956, 1844; Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282; Murphy, W. S.; Bertrand, M. J. Chem. Soc., Perkin Trans. I, 1998, 4115.
    • (1956) J. Chem. Soc. , pp. 1844
    • Andrews, K.J.M.1    Marrian, D.H.2    Maxwell, D.R.3
  • 44
    • 0000486622 scopus 로고
    • Andrews, K. J. M.; Marrian, D. H.; Maxwell, D. R. J. Chem. Soc. 1956, 1844; Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282; Murphy, W. S.; Bertrand, M. J. Chem. Soc., Perkin Trans. I, 1998, 4115.
    • (1985) J. Org. Chem. , vol.50 , pp. 4282
    • Hegedus, L.S.1    Mulhern, T.A.2    Mori, A.3
  • 45
    • 33748735275 scopus 로고    scopus 로고
    • Andrews, K. J. M.; Marrian, D. H.; Maxwell, D. R. J. Chem. Soc. 1956, 1844; Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282; Murphy, W. S.; Bertrand, M. J. Chem. Soc., Perkin Trans. I, 1998, 4115.
    • (1998) J. Chem. Soc., Perkin Trans. I , pp. 4115
    • Murphy, W.S.1    Bertrand, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.