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Volumn 121, Issue 17, 1999, Pages 4155-4167

The reaction of active zinc with organic bromides

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; ZINC;

EID: 0033526370     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9844478     Document Type: Article
Times cited : (84)

References (134)
  • 3
    • 0041338323 scopus 로고
    • Barton, D., Ollis, W. D., Eds.; Pergamon Press: New York
    • (a) Wakefield, B. J. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press: New York, 1979; Vol. 3, pp 944, 974-6.
    • (1979) Comprehensive Organic Chemistry , vol.3 , pp. 944
    • Wakefield, B.J.1
  • 4
    • 0042841052 scopus 로고
    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York
    • (b) Wardell, J. L.; Lindsell, W. E. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 1, pp 52-4 and 156-78, respectively.
    • (1982) Comprehensive Organometallic Chemistry , vol.1 , pp. 52-54
    • Wardell, J.L.1    Lindsell, W.E.2
  • 11
    • 85069280453 scopus 로고    scopus 로고
    • Reference 3a,b
    • (b) Reference 3a,b.
  • 22
  • 23
    • 0032537674 scopus 로고    scopus 로고
    • For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
    • (1998) Tetrahedron , vol.54 , pp. 8275
    • Knochel, P.1    Almena-Perea, J.J.2    Jones, P.3
  • 24
    • 0000618905 scopus 로고    scopus 로고
    • For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
    • (1996) J. Org. Chem. , vol.61 , pp. 2726
    • Rieke, R.D.1    Hanson, M.V.2    Brown, J.D.3
  • 25
    • 0001714999 scopus 로고
    • For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
    • (1995) J. Am. Chem. Sac. , vol.117 , pp. 233
    • Chen, T.-A.1    Wu, X.2    Rieke, R.D.3
  • 26
    • 0000080839 scopus 로고
    • For a recent review, see: (a) Knochel P.; Almena-Perea J. J.; Jones P. Tetrahedron 1998, 54, 8275. For some articles, see: (b) Rieke, R. D.; Hanson, M. V.; Brown, J. D. J. Org. Chem. 1996, 61, 2726. (c) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Sac. 1995, 117, 233. (d) Hanson, M. V.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 10775.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10775
    • Hanson, M.V.1    Rieke, R.D.2
  • 32
    • 85069283772 scopus 로고    scopus 로고
    • Reference 11a
    • (f) Reference 11a.
  • 34
    • 0000512023 scopus 로고
    • For earlier forms of Zn* with lower activity, see: (b) Rieke, R. D.; Li, P. T.; Burns, T. P.; Uhm, S. T. J. Org. Chem. 1981, 46, 4323. (c) Rieke, R. D.; Uhm, S. J.; Hudnall, P. M. J. Chem. Soc., Chem. Commun. 1973, 269.
    • (1981) J. Org. Chem. , vol.46 , pp. 4323
    • Rieke, R.D.1    Li, P.T.2    Burns, T.P.3    Uhm, S.T.4
  • 35
    • 37049138739 scopus 로고
    • For earlier forms of Zn* with lower activity, see: (b) Rieke, R. D.; Li, P. T.; Burns, T. P.; Uhm, S. T. J. Org. Chem. 1981, 46, 4323. (c) Rieke, R. D.; Uhm, S. J.; Hudnall, P. M. J. Chem. Soc., Chem. Commun. 1973, 269.
    • (1973) J. Chem. Soc., Chem. Commun. , pp. 269
    • Rieke, R.D.1    Uhm, S.J.2    Hudnall, P.M.3
  • 36
    • 0003625966 scopus 로고
    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York
    • Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1982; Vol. 2, p 832.
    • (1982) Comprehensive Organometallic Chemistry , vol.2 , pp. 832
    • Boersma, J.1
  • 37
    • 0032479487 scopus 로고    scopus 로고
    • Reported at the 217th National Meeting of the American Chemical Society, Anaheim, CA, March 1999. For a preliminary communication, see: Guijarro, A.; Rieke, R. D. Angew. Chem., Int. Ed. Engl. 1998, 37, 1679.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 1679
    • Guijarro, A.1    Rieke, R.D.2
  • 38
    • 85069281870 scopus 로고
    • Hartley, F. R., Patai, S., Eds.; John Wiley & Sons: Chichester-New York
    • Stille, J. K. In The Chemistry of Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; John Wiley & Sons: Chichester-New York, 1985; Vol. 2, pp 629-630.
    • (1985) The Chemistry of Metal-Carbon Bond , vol.2 , pp. 629-630
    • Stille, J.K.1
  • 39
    • 0344670464 scopus 로고
    • Yao, C.-Y. Diss. Abstr. 1964, 24, 4414; Chem. Abstr. 1964, 61, 6443g.
    • (1964) Diss. Abstr. , vol.24 , pp. 4414
    • Yao, C.-Y.1
  • 40
    • 84915490512 scopus 로고
    • Yao, C.-Y. Diss. Abstr. 1964, 24, 4414; Chem. Abstr. 1964, 61, 6443g.
    • (1964) Chem. Abstr. , vol.61
  • 41
    • 0003911221 scopus 로고
    • Cornell University Press: London
    • Rehybridization of the carbon in the transition state releases strain in cyclopentyl derivatives: Brown, H. C. Boranes in Organic Chemistry; Cornell University Press: London, 1972; pp 105-107, 126-128. In 1-adamantyl derivatives the situation is opposite, due to the rigidity of the backbone.
    • (1972) Boranes in Organic Chemistry , pp. 105-107
    • Brown, H.C.1
  • 42
    • 0004105856 scopus 로고
    • Longman Scientific & Technical: Harlow Essex, England
    • -. Isaacs, N. S. Physical Organic Chemistry; Longman Scientific & Technical: Harlow Essex, England, 1987; pp 380-381.
    • (1987) Physical Organic Chemistry , pp. 380-381
    • Isaacs, N.S.1
  • 43
    • 85069279066 scopus 로고    scopus 로고
    • note
    • Intuitively attributed to some degree of nonreproducible thermal decomposition through the stationary phase.
  • 47
    • 85069280939 scopus 로고    scopus 로고
    • Present paper
    • Present paper.
  • 53
  • 64
    • 0001500051 scopus 로고
    • N2 equilibration such as exo- and endo-7-iodonorearane were found to react with complete loss of their stereochemical integrity: Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. This and the evidence accumulated in this work point to a radical-induced loss of stereochemistry, rather than retention in the reduction step.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5373
    • Luche, J.L.1    Allavena, C.2    Petrier, C.3    Dupuy, C.4
  • 65
    • 0344881536 scopus 로고
    • N2 equilibration such as exo- and endo-7-iodonorearane were found to react with complete loss of their stereochemical integrity: Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. This and the evidence accumulated in this work point to a radical-induced loss of stereochemistry, rather than retention in the reduction step.
    • (1983) J. Org. Chem. , vol.48 , pp. 2233
    • Turecek, F.1    Veres, K.2    Kocovsky, P.3    Pouzar, V.4    Fajkos, J.5
  • 66
    • 0028032063 scopus 로고
    • N2 equilibration such as exo- and endo-7-iodonorearane were found to react with complete loss of their stereochemical integrity: Duddu, R.; Eckhardt, M.; Furlong, M.; Knoess, P.; Berger, S.; Knochel, P. Tetrahedron 1994, 50, 2415. This and the evidence accumulated in this work point to a radical-induced loss of stereochemistry, rather than retention in the reduction step.
    • (1994) Tetrahedron , vol.50 , pp. 2415
    • Duddu, R.1    Eckhardt, M.2    Furlong, M.3    Knoess, P.4    Berger, S.5    Knochel, P.6
  • 74
    • 85069277992 scopus 로고    scopus 로고
    • note
    • No cyclopentanone could be detected by GLC analysis of the hydrolyzed (2 M HCl) crude reaction mixture.
  • 79
    • 85069277323 scopus 로고    scopus 로고
    • note
    • Alignment of the C-X dipole to the potential field gradient near the surface might induce ionization of the bond. This mechanism, suggested in electrochemical reductions, was later discarded: ref 27a, pp 1016-1018.
  • 80
    • 85069282276 scopus 로고    scopus 로고
    • note
    • Bridgehead bicyclic halides, among others, would be expected to be far less reactive: ref 27a, pp 1017-1018.
  • 85
    • 85069280260 scopus 로고    scopus 로고
    • Reference 36, Chapter viii
    • (c) Reference 36, Chapter viii.
  • 89
    • 85069283930 scopus 로고    scopus 로고
    • Reference 36, pp 122-123
    • (c) Reference 36, pp 122-123.
  • 96
    • 0000165414 scopus 로고
    • For example, the Marcus theory for outer-sphere ET was applied to alkyl halide reductions by inner- and outer-sphere reagents with reasonable success: Eberson, L. Acta Chem. Scand. 1982, B36, 533.
    • (1982) Acta Chem. Scand. , vol.B36 , pp. 533
    • Eberson, L.1
  • 97
    • 85069283343 scopus 로고    scopus 로고
    • note
    • p(n-RBr).
  • 100
    • 85069275013 scopus 로고    scopus 로고
    • note
    • 3 ↔ ...] were used to describe the transition state: ref 56.
  • 101
    • 85069283075 scopus 로고    scopus 로고
    • note
    • (b) An outer-sphere ET cannot be totally ruled out: ref 6d.
  • 102
    • 85012331749 scopus 로고
    • •, is an irreversible step. An equilibrium seems reasonable for this step. Indeed, ΔH is only slightly exothermic in these halogen transfers: Nash, G. A.; Skinner, H. A.; Stack, W. F. Trans. Faraday Soc. 1965, 61, 640, 2122. This would explain why this reaction is abnormally positioned toward the right in Figure 2.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 7047
    • Carlsson, D.J.1    Ingold, K.U.2
  • 103
    • 0040976087 scopus 로고
    • •, is an irreversible step. An equilibrium seems reasonable for this step. Indeed, ΔH is only slightly exothermic in these halogen transfers: Nash, G. A.; Skinner, H. A.; Stack, W. F. Trans. Faraday Soc. 1965, 61, 640, 2122. This would explain why this reaction is abnormally positioned toward the right in Figure 2.
    • (1965) Trans. Faraday Soc. , vol.61 , pp. 640
    • Nash, G.A.1    Skinner, H.A.2    Stack, W.F.3
  • 109
    • 85069276143 scopus 로고    scopus 로고
    • Reference 26
    • (b) Reference 26.
  • 110
    • 85069276492 scopus 로고    scopus 로고
    • Reference 37, Chapter vii
    • Reference 37, Chapter vii.
  • 112
    • 0004032955 scopus 로고
    • John Wiley & Sons: New York
    • "The formations of Grignard reagents and organolithium compounds are examples of the reduction of alkyl halides directly by metals.... It is not clear whether inner- or outer-sphere processes are involved since the reactions occurring on a metal surface offer only a limited number of probes": Kochi, J. K. Free Radicals: John Wiley & Sons: New York, 1973; 663.
    • (1973) Free Radicals , pp. 663
    • Kochi, J.K.1
  • 113
    • 85069278331 scopus 로고    scopus 로고
    • note
    • rel plot for both reactions being a measure of the relative selectivity.
  • 114
    • 0003625968 scopus 로고
    • Wilkinson, G., Ed.; Pergamon Press: Oxford-New York
    • (a) Prince, R. H. In Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford-New York, 1987; Vol. 5, pp 983-985.
    • (1987) Comprehensive Coordination Chemistry , vol.5 , pp. 983-985
    • Prince, R.H.1
  • 116
    • 0003730993 scopus 로고
    • McGraw-Hill: New York
    • σ values; (a) Hine, J. Physical Organic Chemistry; McGraw-Hill: New York, 1962. (b) Isaacs, N. S. Physical Organic Chemistry; Longman Scientific & Technical: Harlow Essex, England, 1987.
    • (1962) Physical Organic Chemistry
    • Hine, J.1
  • 117
    • 0004105856 scopus 로고
    • Longman Scientific & Technical: Harlow Essex, England
    • σ values; (a) Hine, J. Physical Organic Chemistry; McGraw-Hill: New York, 1962. (b) Isaacs, N. S. Physical Organic Chemistry; Longman Scientific & Technical: Harlow Essex, England, 1987.
    • (1987) Physical Organic Chemistry
    • Isaacs, N.S.1
  • 118
    • 85069280515 scopus 로고    scopus 로고
    • note
    • Calculated from kinetic data in ref 6c.
  • 124
    • 0001313287 scopus 로고
    • Studies of tin hydride reductions of bridgehead aliphatic halides have been interpretated as indicating little or no charge separation in the transition state: Fort, R. C., Jr.; Hiti, J. J. Org. Chem. 1977, 42, 3968. However, positive slope of the Hammett plot, ρ = 1.4 points toward some participation of ET with partial negative charge generation at the transition state.
    • (1977) J. Org. Chem. , vol.42 , pp. 3968
    • Fort R.C., Jr.1    Hiti, J.2
  • 125
    • 85069276785 scopus 로고    scopus 로고
    • note
    • Electrochemical reductions have been referred to as "compulsory ET processes" and for inert smooth Pt and some C electrodes is assumed to be outer-sphere ET. For a dropping Hg electrode, which is the case considered here, the situation has been discussed: ref 37, p 79.
  • 126
    • 85069275664 scopus 로고    scopus 로고
    • note
    • With some restrictions, see Table 6, footnote g.
  • 130
    • 0026093516 scopus 로고
    • Grinberg, S.; Shaubi, E. Tetrahedron 1991, 47, 2895. The crude reaction mixture was distilled under vacuum, and an intermediate fraction (61% p-isomer/39% o-isomer) was used in the reaction with active zinc.
    • (1991) Tetrahedron , vol.47 , pp. 2895
    • Grinberg, S.1    Shaubi, E.2
  • 131
    • 85069281366 scopus 로고    scopus 로고
    • note
    • The steady-state approximation, applied to eq 4, gave, without the aid of a computer, a reasonable estimate of the distribution of products. Nonetheless, to compare with experimental results, exact numbers were preferred.
  • 132
    • 85069281948 scopus 로고    scopus 로고
    • note
    • 2 ≥ 135 would be required to yield 96% of 9a.


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