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Volumn , Issue 1, 1998, Pages 59-70

Radical cation mechanism of aromatic halogenation by halogens or iodine chloride in 1,1,1,3,3,3-hexafluoropropan-2-ol

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EID: 0005224617     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705393b     Document Type: Article
Times cited : (44)

References (74)
  • 3
    • 5244308775 scopus 로고
    • A. Pross, Adv. Phys. Org. Chem., 1985, 21, 99; A. Pross, Acc. Chem. Res., 1985, 18, 212; S. S. Shaik, Prog. Phys. Org. Chem., 1985, 15, 197; S. S. Shaik, J. Am. Chem. Soc., 1981, 103, 3692.
    • (1985) Adv. Phys. Org. Chem. , vol.21 , pp. 99
    • Pross, A.1
  • 4
    • 0001621079 scopus 로고
    • A. Pross, Adv. Phys. Org. Chem., 1985, 21, 99; A. Pross, Acc. Chem. Res., 1985, 18, 212; S. S. Shaik, Prog. Phys. Org. Chem., 1985, 15, 197; S. S. Shaik, J. Am. Chem. Soc., 1981, 103, 3692.
    • (1985) Acc. Chem. Res. , vol.18 , pp. 212
    • Pross, A.1
  • 5
    • 5244308775 scopus 로고
    • A. Pross, Adv. Phys. Org. Chem., 1985, 21, 99; A. Pross, Acc. Chem. Res., 1985, 18, 212; S. S. Shaik, Prog. Phys. Org. Chem., 1985, 15, 197; S. S. Shaik, J. Am. Chem. Soc., 1981, 103, 3692.
    • (1985) Prog. Phys. Org. Chem. , vol.15 , pp. 197
    • Shaik, S.S.1
  • 6
    • 33845558643 scopus 로고
    • A. Pross, Adv. Phys. Org. Chem., 1985, 21, 99; A. Pross, Acc. Chem. Res., 1985, 18, 212; S. S. Shaik, Prog. Phys. Org. Chem., 1985, 15, 197; S. S. Shaik, J. Am. Chem. Soc., 1981, 103, 3692.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3692
    • Shaik, S.S.1
  • 7
    • 0013234104 scopus 로고
    • Early proposals and refutation: J. Kenner, Nature, 1945, 156, 369; J. Weiss, Trans. Faraday Soc., 1946, 42, 116; G. A. Benford, C. A. Bunton, E. S. Halberstadt, E. D. Hughes, C. K. Ingold and R. E. Reed, Nature, 1945, 156, 688. Revival: C. L. Perrin, J. Am. Chem. Soc., 1977,.99, 5516.
    • (1945) Nature , vol.156 , pp. 369
    • Kenner, J.1
  • 8
    • 37049154810 scopus 로고
    • Early proposals and refutation: J. Kenner, Nature, 1945, 156, 369; J. Weiss, Trans. Faraday Soc., 1946, 42, 116; G. A. Benford, C. A. Bunton, E. S. Halberstadt, E. D. Hughes, C. K. Ingold and R. E. Reed, Nature, 1945, 156, 688. Revival: C. L. Perrin, J. Am. Chem. Soc., 1977,.99, 5516.
    • (1946) Trans. Faraday Soc. , vol.42 , pp. 116
    • Weiss, J.1
  • 9
    • 0010911112 scopus 로고
    • Early proposals and refutation: J. Kenner, Nature, 1945, 156, 369; J. Weiss, Trans. Faraday Soc., 1946, 42, 116; G. A. Benford, C. A. Bunton, E. S. Halberstadt, E. D. Hughes, C. K. Ingold and R. E. Reed, Nature, 1945, 156, 688. Revival: C. L. Perrin, J. Am. Chem. Soc., 1977,.99, 5516.
    • (1945) Nature , vol.156 , pp. 688
    • Benford, G.A.1    Bunton, C.A.2    Halberstadt, E.S.3    Hughes, E.D.4    Ingold, C.K.5    Reed, R.E.6
  • 10
    • 33847089344 scopus 로고
    • Early proposals and refutation: J. Kenner, Nature, 1945, 156, 369; J. Weiss, Trans. Faraday Soc., 1946, 42, 116; G. A. Benford, C. A. Bunton, E. S. Halberstadt, E. D. Hughes, C. K. Ingold and R. E. Reed, Nature, 1945, 156, 688. Revival: C. L. Perrin, J. Am. Chem. Soc., 1977,.99, 5516.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 5516
    • Perrin, C.L.1
  • 13
    • 70450094439 scopus 로고
    • See, for example: A. J. Bard, A. Ledwith and H. J. Shine, Adv. Phys. Org. Chem., 1976, 12, 155; F. M. Dean and U. Oyman, Tetrahedron Lett., 1988, 3721; F. M. Dean, S. N. France and U. Oyman, Tetrahedron, 1988, 44, 4857; M. V. Jovanovic and E. R. Biehl, J. Org. Chem., 1984, 49, 1905; H. Chiou, P. C. Reeves and E. R. Biehl, J. Heterocycl. Chem., 1976, 13, 77; F. Effenberger, P. Bäuerle, W. Seufert and W.-D. Stohrer, Chem. Ber., 1990, 123, 193.
    • (1976) Adv. Phys. Org. Chem. , vol.12 , pp. 155
    • Bard, A.J.1    Ledwith, A.2    Shine, H.J.3
  • 14
    • 0038663389 scopus 로고
    • See, for example: A. J. Bard, A. Ledwith and H. J. Shine, Adv. Phys. Org. Chem., 1976, 12, 155; F. M. Dean and U. Oyman, Tetrahedron Lett., 1988, 3721; F. M. Dean, S. N. France and U. Oyman, Tetrahedron, 1988, 44, 4857; M. V. Jovanovic and E. R. Biehl, J. Org. Chem., 1984, 49, 1905; H. Chiou, P. C. Reeves and E. R. Biehl, J. Heterocycl. Chem., 1976, 13, 77; F. Effenberger, P. Bäuerle, W. Seufert and W.-D. Stohrer, Chem. Ber., 1990, 123, 193.
    • (1988) Tetrahedron Lett. , pp. 3721
    • Dean, F.M.1    Oyman, U.2
  • 15
    • 0038663390 scopus 로고
    • See, for example: A. J. Bard, A. Ledwith and H. J. Shine, Adv. Phys. Org. Chem., 1976, 12, 155; F. M. Dean and U. Oyman, Tetrahedron Lett., 1988, 3721; F. M. Dean, S. N. France and U. Oyman, Tetrahedron, 1988, 44, 4857; M. V. Jovanovic and E. R. Biehl, J. Org. Chem., 1984, 49, 1905; H. Chiou, P. C. Reeves and E. R. Biehl, J. Heterocycl. Chem., 1976, 13, 77; F. Effenberger, P. Bäuerle, W. Seufert and W.-D. Stohrer, Chem. Ber., 1990, 123, 193.
    • (1988) Tetrahedron , vol.44 , pp. 4857
    • Dean, F.M.1    France, S.N.2    Oyman, U.3
  • 16
    • 0021278864 scopus 로고
    • See, for example: A. J. Bard, A. Ledwith and H. J. Shine, Adv. Phys. Org. Chem., 1976, 12, 155; F. M. Dean and U. Oyman, Tetrahedron Lett., 1988, 3721; F. M. Dean, S. N. France and U. Oyman, Tetrahedron, 1988, 44, 4857; M. V. Jovanovic and E. R. Biehl, J. Org. Chem., 1984, 49, 1905; H. Chiou, P. C. Reeves and E. R. Biehl, J. Heterocycl. Chem., 1976, 13, 77; F. Effenberger, P. Bäuerle, W. Seufert and W.-D. Stohrer, Chem. Ber., 1990, 123, 193.
    • (1984) J. Org. Chem. , vol.49 , pp. 1905
    • Jovanovic, M.V.1    Biehl, E.R.2
  • 17
    • 84980258550 scopus 로고
    • See, for example: A. J. Bard, A. Ledwith and H. J. Shine, Adv. Phys. Org. Chem., 1976, 12, 155; F. M. Dean and U. Oyman, Tetrahedron Lett., 1988, 3721; F. M. Dean, S. N. France and U. Oyman, Tetrahedron, 1988, 44, 4857; M. V. Jovanovic and E. R. Biehl, J. Org. Chem., 1984, 49, 1905; H. Chiou, P. C. Reeves and E. R. Biehl, J. Heterocycl. Chem., 1976, 13, 77; F. Effenberger, P. Bäuerle, W. Seufert and W.-D. Stohrer, Chem. Ber., 1990, 123, 193.
    • (1976) J. Heterocycl. Chem. , vol.13 , pp. 77
    • Chiou, H.1    Reeves, P.C.2    Biehl, E.R.3
  • 18
    • 84984351672 scopus 로고
    • See, for example: A. J. Bard, A. Ledwith and H. J. Shine, Adv. Phys. Org. Chem., 1976, 12, 155; F. M. Dean and U. Oyman, Tetrahedron Lett., 1988, 3721; F. M. Dean, S. N. France and U. Oyman, Tetrahedron, 1988, 44, 4857; M. V. Jovanovic and E. R. Biehl, J. Org. Chem., 1984, 49, 1905; H. Chiou, P. C. Reeves and E. R. Biehl, J. Heterocycl. Chem., 1976, 13, 77; F. Effenberger, P. Bäuerle, W. Seufert and W.-D. Stohrer, Chem. Ber., 1990, 123, 193.
    • (1990) Chem. Ber. , vol.123 , pp. 193
    • Effenberger, F.1    Bäuerle, P.2    Seufert, W.3    Stohrer, W.-D.4
  • 29
    • 0001463080 scopus 로고    scopus 로고
    • A study of the bromination of 4,4′-dimethoxystilbene in 1,2-dichloromethane was recently published: G. Bellucci, C. Chiappe and G. Lo Moro, J. Org. Chem., 1997, 62, 3176.
    • (1997) J. Org. Chem. , vol.62 , pp. 3176
    • Bellucci, G.1    Chiappe, C.2    Lo Moro, G.3
  • 39
    • 0347009326 scopus 로고    scopus 로고
    • In view of the reaction course shown for 1-ICl in Fig. 5, the kinetics of the reactions of 3 and 4 should be accessible by the stopped-flow method
    • In view of the reaction course shown for 1-ICl in Fig. 5, the kinetics of the reactions of 3 and 4 should be accessible by the stopped-flow method.
  • 42
    • 0347640133 scopus 로고    scopus 로고
    • .+ in dichloromethane (ref. 7c)
    • .+ in dichloromethane (ref. 7c).
  • 52
    • 0347009322 scopus 로고    scopus 로고
    • It may be argued that chlorination may also result from the action of chlorine, present in equilibrium with ICl and iodine (see note 22 in ref. 7c). However, in HFP chlorination of 4 and compounds of similar reactivity would take place via the ET mechanism
    • It may be argued that chlorination may also result from the action of chlorine, present in equilibrium with ICl and iodine (see note 22 in ref. 7c). However, in HFP chlorination of 4 and compounds of similar reactivity would take place via the ET mechanism.
  • 53
    • 0002672933 scopus 로고
    • ed. J. S. Pizey, Harwood, Chichester
    • C. W. McCleland, Synthetic Reagents, ed. J. S. Pizey, Harwood, Chichester, 1983, vol. 5, p. 85.
    • (1983) Synthetic Reagents , vol.5 , pp. 85
    • McCleland, C.W.1
  • 55
    • 0013056822 scopus 로고    scopus 로고
    • National Institute of Environmental Health Sciences
    • D. Duling, Public EPR Software Tools, National Institute of Environmental Health Sciences, 1996.
    • (1996) Public EPR Software Tools
    • Duling, D.1
  • 56
    • 0346379325 scopus 로고    scopus 로고
    • It is advisable to use the best HFP qualities commercially available, since the cheaper qualities may have hydrogen fluoride as an impurity
    • It is advisable to use the best HFP qualities commercially available, since the cheaper qualities may have hydrogen fluoride as an impurity.
  • 68
    • 0347640131 scopus 로고
    • P. D. Sullivan and N. A. Brette, J. Phys. Chem., 1975, 79, 474; P. D. Sullivan, J. Am. Chem. Soc., 1975, 97, 3992.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 3992
    • Sullivan, P.D.1
  • 70
    • 0025743797 scopus 로고
    • L. Eberson and F. Radner, J. Chem. Soc., Chem. Commun., 1991, 1233; Acta Chem. Scand., 1992, 46, 630.
    • (1992) Acta Chem. Scand. , vol.46 , pp. 630


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