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Volumn 37, Issue 22, 1998, Pages 3173-3175

An unprecedented elimination-driven migration: The reductive dihalobornane-camphene rearrangement

Author keywords

Eliminations; Fragmentations; Intermediates; Reaction mechanisms; Rearrangements

Indexed keywords

BROMINE; CAMPHENE; TERPENE;

EID: 0032484057     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981204)37:22<3173::AID-ANIE3173>3.0.CO;2-Y     Document Type: Article
Times cited : (5)

References (34)
  • 1
    • 0344636989 scopus 로고
    • J. F. Bunnett, Angew. Chem. 1962, 74, 131-741; Angew. Chem. Int. Ed. Engl. 1962, 1, 225-235; J. Sicher, Angew. Chem. 1972, 84, 177-191; Angew. Chem. Int. Ed. Engl. 1972, 11, 200-214; M. Schlosser, Methoden Org. Chem. (Houben-Weyl) 4. ed. 1952-, Vol. 5/1b, pp. 9-44.
    • (1962) Angew. Chem. , vol.74 , pp. 131-741
    • Bunnett, J.F.1
  • 2
    • 3042772726 scopus 로고
    • J. F. Bunnett, Angew. Chem. 1962, 74, 131-741; Angew. Chem. Int. Ed. Engl. 1962, 1, 225-235; J. Sicher, Angew. Chem. 1972, 84, 177-191; Angew. Chem. Int. Ed. Engl. 1972, 11, 200-214; M. Schlosser, Methoden Org. Chem. (Houben-Weyl) 4. ed. 1952-, Vol. 5/1b, pp. 9-44.
    • (1962) Angew. Chem. Int. Ed. Engl. , vol.1 , pp. 225-235
  • 3
    • 0345725742 scopus 로고
    • J. F. Bunnett, Angew. Chem. 1962, 74, 131-741; Angew. Chem. Int. Ed. Engl. 1962, 1, 225-235; J. Sicher, Angew. Chem. 1972, 84, 177-191; Angew. Chem. Int. Ed. Engl. 1972, 11, 200-214; M. Schlosser, Methoden Org. Chem. (Houben-Weyl) 4. ed. 1952-, Vol. 5/1b, pp. 9-44.
    • (1972) Angew. Chem. , vol.84 , pp. 177-191
    • Sicher, J.1
  • 4
    • 84981922386 scopus 로고
    • J. F. Bunnett, Angew. Chem. 1962, 74, 131-741; Angew. Chem. Int. Ed. Engl. 1962, 1, 225-235; J. Sicher, Angew. Chem. 1972, 84, 177-191; Angew. Chem. Int. Ed. Engl. 1972, 11, 200-214; M. Schlosser, Methoden Org. Chem. (Houben-Weyl) 4. ed. 1952-, Vol. 5/1b, pp. 9-44.
    • (1972) Angew. Chem. Int. Ed. Engl. , vol.11 , pp. 200-214
  • 5
    • 0345067633 scopus 로고
    • J. F. Bunnett, Angew. Chem. 1962, 74, 131-741; Angew. Chem. Int. Ed. Engl. 1962, 1, 225-235; J. Sicher, Angew. Chem. 1972, 84, 177-191; Angew. Chem. Int. Ed. Engl. 1972, 11, 200-214; M. Schlosser, Methoden Org. Chem. (Houben-Weyl) 4. ed. 1952-, Vol. 5/1b, pp. 9-44.
    • (1952) Methoden Org. Chem. (Houben-Weyl) 4. Ed. , vol.5 , Issue.1 B , pp. 9-44
    • Schlosser, M.1
  • 6
    • 0000703627 scopus 로고
    • R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853; M. J. S. Dewar, Angew. Chem. 1971, 83, 859-875; Angew. Chem. Int. Ed. Engl. 1971, 10, 761-775.
    • (1969) Angew. Chem. , vol.81 , pp. 797-869
    • Woodward, R.B.1    Hoffmann, R.2
  • 7
    • 84981778017 scopus 로고
    • R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853; M. J. S. Dewar, Angew. Chem. 1971, 83, 859-875; Angew. Chem. Int. Ed. Engl. 1971, 10, 761-775.
    • (1969) Angew. Chem. Int. Ed. Engl. , vol.8 , pp. 781-853
  • 8
    • 0011562234 scopus 로고
    • R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853; M. J. S. Dewar, Angew. Chem. 1971, 83, 859-875; Angew. Chem. Int. Ed. Engl. 1971, 10, 761-775.
    • (1971) Angew. Chem. , vol.83 , pp. 859-875
    • Dewar, M.J.S.1
  • 9
    • 84981890433 scopus 로고
    • R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869; Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853; M. J. S. Dewar, Angew. Chem. 1971, 83, 859-875; Angew. Chem. Int. Ed. Engl. 1971, 10, 761-775.
    • (1971) Angew. Chem. Int. Ed. Engl. , vol.10 , pp. 761-775
  • 10
    • 0013574861 scopus 로고
    • J. Feuer, W. C. Herndon, L. H. Hall, Tetrahedron 1968, 24, 2575-2582; N. D. Epiotis, J. Am. Chem. Soc. 1973, 95, 5624-5632; K. N. Houk, Acc. Chem. Res. 1975, 8, 361-369; I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York 1976; I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990; K. Fukui, Angew. Chem. 1982, 94, 852-861; Angew. Chem. Int. Ed. Engl. 1982, 21, 801-809.
    • (1968) Tetrahedron , vol.24 , pp. 2575-2582
    • Feuer, J.1    Herndon, W.C.2    Hall, L.H.3
  • 11
    • 0009983447 scopus 로고
    • J. Feuer, W. C. Herndon, L. H. Hall, Tetrahedron 1968, 24, 2575-2582; N. D. Epiotis, J. Am. Chem. Soc. 1973, 95, 5624-5632; K. N. Houk, Acc. Chem. Res. 1975, 8, 361-369; I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York 1976; I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990; K. Fukui, Angew. Chem. 1982, 94, 852-861; Angew. Chem. Int. Ed. Engl. 1982, 21, 801-809.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 5624-5632
    • Epiotis, N.D.1
  • 12
    • 0346888810 scopus 로고
    • J. Feuer, W. C. Herndon, L. H. Hall, Tetrahedron 1968, 24, 2575-2582; N. D. Epiotis, J. Am. Chem. Soc. 1973, 95, 5624-5632; K. N. Houk, Acc. Chem. Res. 1975, 8, 361-369; I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York 1976; I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990; K. Fukui, Angew. Chem. 1982, 94, 852-861; Angew. Chem. Int. Ed. Engl. 1982, 21, 801-809.
    • (1975) Acc. Chem. Res. , vol.8 , pp. 361-369
    • Houk, K.N.1
  • 13
    • 0003787137 scopus 로고
    • Wiley, New York
    • J. Feuer, W. C. Herndon, L. H. Hall, Tetrahedron 1968, 24, 2575-2582; N. D. Epiotis, J. Am. Chem. Soc. 1973, 95, 5624-5632; K. N. Houk, Acc. Chem. Res. 1975, 8, 361-369; I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York 1976; I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990; K. Fukui, Angew. Chem. 1982, 94, 852-861; Angew. Chem. Int. Ed. Engl. 1982, 21, 801-809.
    • (1976) Frontier Orbitals and Organic Chemical Reactions
    • Fleming, I.1
  • 14
    • 0003539395 scopus 로고
    • VCH, Weinheim
    • J. Feuer, W. C. Herndon, L. H. Hall, Tetrahedron 1968, 24, 2575-2582; N. D. Epiotis, J. Am. Chem. Soc. 1973, 95, 5624-5632; K. N. Houk, Acc. Chem. Res. 1975, 8, 361-369; I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York 1976; I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990; K. Fukui, Angew. Chem. 1982, 94, 852-861; Angew. Chem. Int. Ed. Engl. 1982, 21, 801-809.
    • (1990) Grenzorbitale und Reaktionen Organischer Verbindungen
    • Fleming, I.1
  • 15
    • 0005392239 scopus 로고
    • J. Feuer, W. C. Herndon, L. H. Hall, Tetrahedron 1968, 24, 2575-2582; N. D. Epiotis, J. Am. Chem. Soc. 1973, 95, 5624-5632; K. N. Houk, Acc. Chem. Res. 1975, 8, 361-369; I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York 1976; I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990; K. Fukui, Angew. Chem. 1982, 94, 852-861; Angew. Chem. Int. Ed. Engl. 1982, 21, 801-809.
    • (1982) Angew. Chem. , vol.94 , pp. 852-861
    • Fukui, K.1
  • 16
    • 84985502129 scopus 로고
    • J. Feuer, W. C. Herndon, L. H. Hall, Tetrahedron 1968, 24, 2575-2582; N. D. Epiotis, J. Am. Chem. Soc. 1973, 95, 5624-5632; K. N. Houk, Acc. Chem. Res. 1975, 8, 361-369; I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York 1976; I. Fleming, Grenzorbitale und Reaktionen organischer Verbindungen, VCH, Weinheim, 1990; K. Fukui, Angew. Chem. 1982, 94, 852-861; Angew. Chem. Int. Ed. Engl. 1982, 21, 801-809.
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 801-809
  • 17
    • 0345067630 scopus 로고
    • M. Geisel, C. A. Grob, R. A. Wohl, Helv. Chim. Acta 1969, 52, 2206-2215; C. A. Grob, P. W. Schiess, Angew. Chem. 1967, 79, 1-14; Angew. Chem. Int. Ed. Engl. 1967, 6, 1-15; C. A. Grob, Angew. Chem. 1969, 81, 543-554; Angew. Chem. Int. Ed. Engl. 1969, 8, 535-546.
    • (1969) Helv. Chim. Acta , vol.52 , pp. 2206-2215
    • Geisel, M.1    Grob, C.A.2    Wohl, R.A.3
  • 18
    • 0001836768 scopus 로고
    • M. Geisel, C. A. Grob, R. A. Wohl, Helv. Chim. Acta 1969, 52, 2206-2215; C. A. Grob, P. W. Schiess, Angew. Chem. 1967, 79, 1-14; Angew. Chem. Int. Ed. Engl. 1967, 6, 1-15; C. A. Grob, Angew. Chem. 1969, 81, 543-554; Angew. Chem. Int. Ed. Engl. 1969, 8, 535-546.
    • (1967) Angew. Chem. , vol.79 , pp. 1-14
    • Grob, C.A.1    Schiess, P.W.2
  • 19
    • 0038459812 scopus 로고
    • M. Geisel, C. A. Grob, R. A. Wohl, Helv. Chim. Acta 1969, 52, 2206-2215; C. A. Grob, P. W. Schiess, Angew. Chem. 1967, 79, 1-14; Angew. Chem. Int. Ed. Engl. 1967, 6, 1-15; C. A. Grob, Angew. Chem. 1969, 81, 543-554; Angew. Chem. Int. Ed. Engl. 1969, 8, 535-546.
    • (1967) Angew. Chem. Int. Ed. Engl. , vol.6 , pp. 1-15
  • 20
    • 0001136403 scopus 로고
    • M. Geisel, C. A. Grob, R. A. Wohl, Helv. Chim. Acta 1969, 52, 2206-2215; C. A. Grob, P. W. Schiess, Angew. Chem. 1967, 79, 1-14; Angew. Chem. Int. Ed. Engl. 1967, 6, 1-15; C. A. Grob, Angew. Chem. 1969, 81, 543-554; Angew. Chem. Int. Ed. Engl. 1969, 8, 535-546.
    • (1969) Angew. Chem. , vol.81 , pp. 543-554
    • Grob, C.A.1
  • 21
    • 84981784630 scopus 로고
    • M. Geisel, C. A. Grob, R. A. Wohl, Helv. Chim. Acta 1969, 52, 2206-2215; C. A. Grob, P. W. Schiess, Angew. Chem. 1967, 79, 1-14; Angew. Chem. Int. Ed. Engl. 1967, 6, 1-15; C. A. Grob, Angew. Chem. 1969, 81, 543-554; Angew. Chem. Int. Ed. Engl. 1969, 8, 535-546.
    • (1969) Angew. Chem. Int. Ed. Engl. , vol.8 , pp. 535-546
  • 23
    • 84982472849 scopus 로고
    • For the reversibility of the ring closure of 5-hexenyl metal compounds to cyclopentylmethyl metal compounds, see A. Maercker, R. Geuss, Chem. Ber. 1973, 106, 773-797; see also M. Newcomb, M. T. Burchill, Tetrahedron Lett. 1982, 23, 4867-4870; W. H. Bailey, L. M. J. Zarcone, Tetrahedron Lett. 1991, 32, 4425-4426.
    • (1973) Chem. Ber. , vol.106 , pp. 773-797
    • Maercker, A.1    Geuss, R.2
  • 24
    • 0345499127 scopus 로고
    • For the reversibility of the ring closure of 5-hexenyl metal compounds to cyclopentylmethyl metal compounds, see A. Maercker, R. Geuss, Chem. Ber. 1973, 106, 773-797; see also M. Newcomb, M. T. Burchill, Tetrahedron Lett. 1982, 23, 4867-4870; W. H. Bailey, L. M. J. Zarcone, Tetrahedron Lett. 1991, 32, 4425-4426.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 4867-4870
    • Newcomb, M.1    Burchill, M.T.2
  • 25
    • 0025873262 scopus 로고
    • For the reversibility of the ring closure of 5-hexenyl metal compounds to cyclopentylmethyl metal compounds, see A. Maercker, R. Geuss, Chem. Ber. 1973, 106, 773-797; see also M. Newcomb, M. T. Burchill, Tetrahedron Lett. 1982, 23, 4867-4870; W. H. Bailey, L. M. J. Zarcone, Tetrahedron Lett. 1991, 32, 4425-4426.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4425-4426
    • Bailey, W.H.1    Zarcone, L.M.J.2
  • 27
    • 0040981211 scopus 로고
    • Wiley, New York
    • Molecular Rearrangements, Vol. 1 and 2 (Ed.: P. DeMayo), Wiley, New York, 1963 and 1964; L. M. Harwood, Polar Rearrangements, University Press, Oxford, 1992.
    • (1963) Molecular Rearrangements , vol.1-2
    • DeMayo, P.1
  • 28
    • 0004052210 scopus 로고
    • University Press, Oxford
    • Molecular Rearrangements, Vol. 1 and 2 (Ed.: P. DeMayo), Wiley, New York, 1963 and 1964; L. M. Harwood, Polar Rearrangements, University Press, Oxford, 1992.
    • (1992) Polar Rearrangements
    • Harwood, L.M.1
  • 30
    • 0003163034 scopus 로고
    • J. A. Berson, Angew. Chem. 1968, 80, 765-777: Angew. Chem. Int. Ed. Engl. 1968, 7, 779-791; J. A. Berson, Annu. Rev. Phys. Chem. 1977, 28, 111-132.
    • (1968) Angew. Chem. , vol.80 , pp. 765-777
    • Berson, J.A.1
  • 31
    • 84981773788 scopus 로고
    • J. A. Berson, Angew. Chem. 1968, 80, 765-777: Angew. Chem. Int. Ed. Engl. 1968, 7, 779-791; J. A. Berson, Annu. Rev. Phys. Chem. 1977, 28, 111-132.
    • (1968) Angew. Chem. Int. Ed. Engl. , vol.7 , pp. 779-791
  • 32
    • 0042573619 scopus 로고
    • J. A. Berson, Angew. Chem. 1968, 80, 765-777: Angew. Chem. Int. Ed. Engl. 1968, 7, 779-791; J. A. Berson, Annu. Rev. Phys. Chem. 1977, 28, 111-132.
    • (1977) Annu. Rev. Phys. Chem. , vol.28 , pp. 111-132
    • Berson, J.A.1
  • 34
    • 84980178669 scopus 로고
    • D. Lenoir, Chem. Ber. 1975, 108, 2055-2072.
    • (1975) Chem. Ber. , vol.108 , pp. 2055-2072
    • Lenoir, D.1


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