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Volumn 63, Issue 9, 1998, Pages 3041-3044

Hammett ρ+ Values as Kinetic Evidence for the Concerted Biomimetic Bicyclization Mechanism

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EID: 0008645980     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972237s     Document Type: Article
Times cited : (8)

References (34)
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    • For a recent review on enzymatic cyclization of squalene and oxidosqualene, see: Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189-2206.
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  • 2
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    • For reviews on polyene cyclizations, see: (a) Taylor, S. K. Org. Prep. Proced. Int. 1992, 24, 245-284. (b) Sutherland, J. K. In Compehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 341-377. (c) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 341-409.
    • (1992) Org. Prep. Proced. Int. , vol.24 , pp. 245-284
    • Taylor, S.K.1
  • 3
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    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
    • For reviews on polyene cyclizations, see: (a) Taylor, S. K. Org. Prep. Proced. Int. 1992, 24, 245-284. (b) Sutherland, J. K. In Compehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 341-377. (c) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 341-409.
    • (1991) Compehensive Organic Synthesis , vol.3 , pp. 341-377
    • Sutherland, J.K.1
  • 4
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    • Morrison, J. D., Ed.; Academic Press: New York
    • For reviews on polyene cyclizations, see: (a) Taylor, S. K. Org. Prep. Proced. Int. 1992, 24, 245-284. (b) Sutherland, J. K. In Compehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 341-377. (c) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 341-409.
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  • 5
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    • and references therein
    • For a review on kinetic approach to the mechanism of cationic polyolefinic cyclization, see: Borčić, S.; Kronja, O.; Humski, K. Croat. Chem. Acta 1994, 67, 171-188 and references therein.
    • (1994) Croat. Chem. Acta , vol.67 , pp. 171-188
    • Borčić, S.1    Kronja, O.2    Humski, K.3
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    • and references therein
    • (a) van Tamelen, E. E. J. Am. Chem. Soc. 1982, 104, 6480-6481 and references therein.
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    • Longman: London, Singapore
    • For reviews, see: (a) Isaacs, N. Physical Organic Chemistry, 2nd ed.; Longman: London, Singapore, 1995; pp 146-192, 451-455, 650-654. See also: (b) Ruasse, M.-F.; Argile, A.; Dubois, J.-E. J. Am. Chem. Soc. 1984, 106, 4846-4849. (c) Hammett, L. P. Physical Organic Chemistry; McGraw-Hill: New York, 1970. Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979-4987.
    • (1995) Physical Organic Chemistry, 2nd Ed. , pp. 146-192
    • Isaacs, N.1
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    • For reviews, see: (a) Isaacs, N. Physical Organic Chemistry, 2nd ed.; Longman: London, Singapore, 1995; pp 146-192, 451-455, 650-654. See also: (b) Ruasse, M.-F.; Argile, A.; Dubois, J.-E. J. Am. Chem. Soc. 1984, 106, 4846-4849. (c) Hammett, L. P. Physical Organic Chemistry; McGraw-Hill: New York, 1970. Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979-4987.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4846-4849
    • Ruasse, M.-F.1    Argile, A.2    Dubois, J.-E.3
  • 20
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    • McGraw-Hill: New York
    • For reviews, see: (a) Isaacs, N. Physical Organic Chemistry, 2nd ed.; Longman: London, Singapore, 1995; pp 146-192, 451-455, 650-654. See also: (b) Ruasse, M.-F.; Argile, A.; Dubois, J.-E. J. Am. Chem. Soc. 1984, 106, 4846-4849. (c) Hammett, L. P. Physical Organic Chemistry; McGraw-Hill: New York, 1970. Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979-4987.
    • (1970) Physical Organic Chemistry
    • Hammett, L.P.1
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    • For reviews, see: (a) Isaacs, N. Physical Organic Chemistry, 2nd ed.; Longman: London, Singapore, 1995; pp 146-192, 451-455, 650-654. See also: (b) Ruasse, M.-F.; Argile, A.; Dubois, J.-E. J. Am. Chem. Soc. 1984, 106, 4846-4849. (c) Hammett, L. P. Physical Organic Chemistry; McGraw-Hill: New York, 1970. Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979-4987.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 4979-4987
    • Brown, H.C.1    Okamoto, Y.2
  • 23
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    • ‡ as that for 1, whose rate can be followed at conventional temperatures by conventional methods
    • ‡ as that for 1, whose rate can be followed at conventional temperatures by conventional methods.
  • 33
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    • and ref 8 cited therein
    • van Tamelen, E. E. Acc. Chem. Res. 1968, 1, 111-120 and ref 8 cited therein.
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    • Van Tamelen, E.E.1


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