Mechanistic evaluation of the halocyclization of 4-penten-1-ol by some bis(2-substituted pyridine) and bis(2,6-disubstituted pyridine)bromonium triflates

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5653-5658

  Cui, Xi Lin ^a   Brown, R S ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; VALERIC ACID DERIVATIVE;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DISSOCIATION CONSTANT; ENANTIOMER; HALOGENATION; REACTION ANALYSIS;

EID: 0033832540     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000449a     Document Type: Article

References (19)

1. (a) Brown, R. S.; Nagorski, R. W.; Bennet, A. J.; McClung, R. E. D.; Aarts, G. H. M.; Klobukowski, M.; McDonald, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1994, 116, 2448.
2. (b) Neverov, A. A.; Muise, T. A.; Brown, R. S. Can. J. Chem. 1997, 75, 1844.
3. (c) Neverov, A. A.; Brown, R. S. J. Org. Chem. 1996, 61, 962.
4. Neverov, A. A.; Brown, R. S. J. Org. Chem. 1998, 63, 5977.
5. (a) Homsi, F.; Rousseau, G. J. Org. Chem. 1999, 64, 81;
6. (b) Tetrahedron Lett. 1999, 1495;
7. (c) J. Org. Chem. 1998, 63, 5255.
8. (d) Simonot, B.; Rouseau, G. J. Org. Chem. 1993, 58, 4.
9. (e) Evans, R. D.; Magee, J. W.; Sclauble, J. H. Synthesis 1988, 862, and references therein.
10. Chamberlin, A. R.; Mulholland, R. L.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672 and references therein.
11. Perrin, D. D.; Armagero, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd ed.; Pergamon Press: Oxford 1980; p 204.
12. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.-i.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
13. Brunner, H.; Storiko, R.; Nuber, B. Tetrahedron: Asymmetry 1998, 9, 407.
14. Smith, J. G.; Wright, G. F. J. Org. Chem. 1952, 17, 1116.
15. D > 2.0 for a normal primary effect. For a discussion of fractionation factor analysis, see: (a) Schowen, R. L. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, 1977. (b) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 1-60. (c) Kresge, A. J.; More-O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 177-274. (d) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Vol.7., Elsevier: Amsterdam, 1987; pp 1-60. (e) Kresge, A. J. J. Am. Chem. Soc. 1973, 95, 3065.
16. D > 2.0 for a normal primary effect. For a discussion of fractionation factor analysis, see: (a) Schowen, R. L. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, 1977. (b) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 1-60. (c) Kresge, A. J.; More-O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 177-274. (d) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Vol.7., Elsevier: Amsterdam, 1987; pp 1-60. (e) Kresge, A. J. J. Am. Chem. Soc. 1973, 95, 3065.
17. D > 2.0 for a normal primary effect. For a discussion of fractionation factor analysis, see: (a) Schowen, R. L. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, 1977. (b) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 1-60. (c) Kresge, A. J.; More-O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 177-274. (d) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Vol.7., Elsevier: Amsterdam, 1987; pp 1-60. (e) Kresge, A. J. J. Am. Chem. Soc. 1973, 95, 3065.
18. D > 2.0 for a normal primary effect. For a discussion of fractionation factor analysis, see: (a) Schowen, R. L. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, 1977. (b) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 1-60. (c) Kresge, A. J.; More-O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 177-274. (d) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Vol.7., Elsevier: Amsterdam, 1987; pp 1-60. (e) Kresge, A. J. J. Am. Chem. Soc. 1973, 95, 3065.
19. D > 2.0 for a normal primary effect. For a discussion of fractionation factor analysis, see: (a) Schowen, R. L. In Isotope Effects on Enzyme-Catalyzed Reactions; Cleland, W. W., O'Leary, M. H., Northrop, D. B., Eds.; University Park Press: Baltimore, 1977. (b) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 1-60. (c) Kresge, A. J.; More-O'Ferrall, R. A.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: Amsterdam, 1987; Vol. 7, pp 177-274. (d) Alvarez, F. J.; Schowen, R. L. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Vol.7., Elsevier: Amsterdam, 1987; pp 1-60. (e) Kresge, A. J. J. Am. Chem. Soc. 1973, 95, 3065.