Substituent effects on intramolecular epoxide cyclizations that can competitively occur at aromatic or double bond positions

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 2075-2080

  Taylor, Stephen K ^a   May, Scott A ^a   Stansby, Eric S ^a  

^a HOPE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC GROUP; COMPLEX PRODUCTS; CYCLIZATIONS; DOUBLE BOND POSITIONS; DOUBLE BONDS; SUBSTITUENT EFFECT; TRANSITION STATE;

AROMATIC COMPOUNDS; AROMATIZATION;

CYCLIZATION;

EID: 0001490847     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951945f     Document Type: Article

References (22)

1. A preliminary account of some of this work has been published: Taylor, S. K.; May, S. A.; Hopkins, J. A. Tetrahedron Lett. 1993, 34, 1283.
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3. For earlier reviews see (b) van Tamelen, E. E. Acc. Chem. Res. 1968, 1, 111.
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8. See correction: Ibid. 1991, 56, 5736.
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10. (b) Taylor, S. K.; Davisson, M. E.; Hissom, B. R., Jr.; Brown, S. L.; Pristach, H. A.; Schramm, S. B.; Harvey, S. M. Ibid. 1987, 52, 425.
11. (c) Taylor, S. K.; Bankespoor, C. L.; Harvey, S. M.; Richardson, L. J. J. Org. Chem. 1988, 53, 3309.
12. (a) Broka, C. A.; Chan, S.; Peterson, B. Ibid. 1988, 53, 1586.
13. (b) Burnell, R. H.; Dufour, J. M. Can. J. Chem. 1987, 65, 21.
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15. (b) Tanis, S. P.; Raggon, J. W. Ibid. 1987, 52, 819.
16. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734. For epoxide cyclizations, the exo cyclization results in ring formation with the resulting OH group outside the ring formed. Endo cyclizations result in the OH in the ring formed.
17. Products 10 and 11 account for 81% of the volatile product distribution of eq 2. Products analogous to those represented by the structure below account for another 9% as shown by GCMS and an NMR of the mixture of isomers. We were unable to separate these isomers, but they would be expected to accompany 10 and 12. (Chemical Equation Presented)
18. The yields of these products were undoubtedly higher, but these are the yields of pure, isolated compounds. Impure chromatographic fractions containing these compounds were not counted in the yields.
19. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York, 1987; pp 541-545.
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