Ab initio study of intramolecular ring cyclization of protonated and BF3-coordinated trans- and cis-4,5-epoxyhexan-1-ol

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5530-5541

  Coxon, James M ^a   Thorpe, Aaron J ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

4,5 EPOXYHEXAN 1 OL; EPOXIDE; FURAN DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CIS TRANS ISOMERISM; CYCLIZATION; DRUG CONFORMATION; DRUG STRUCTURE; GEOMETRY; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 0033597738     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990364d     Document Type: Article

References (28)

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5. No tetrahydrofuran could be detected in the product.
6. 2
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8. An alternative theozyme has been determined that favors pyran formation over furan formation consistent with the antibody result. Thorpe, A. PhD Thesis, University of Canterbury, 1999. Coxon, J. M.; Thorpe, A. J., submitted for publication.
9. An alternative theozyme has been determined that favors pyran formation over furan formation consistent with the antibody result. Thorpe, A. PhD Thesis, University of Canterbury, 1999. Coxon, J. M.; Thorpe, A. J., submitted for publication.
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11. This preference was subsequently encapsulated in the rules for ring closure enunciated by Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734. See also Norman, R.; Coxon, J. M. Principles of Organic Synthesis; Blackie Chapman and Hall: London and John Wiley and Sons: New York, 1993; p 678. Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 19, 2939.
12. This preference was subsequently encapsulated in the rules for ring closure enunciated by Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734. See also Norman, R.; Coxon, J. M. Principles of Organic Synthesis; Blackie Chapman and Hall: London and John Wiley and Sons: New York, 1993; p 678. Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 19, 2939.
13. This preference was subsequently encapsulated in the rules for ring closure enunciated by Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734. See also Norman, R.; Coxon, J. M. Principles of Organic Synthesis; Blackie Chapman and Hall: London and John Wiley and Sons: New York, 1993; p 678. Baldwin, J. E.; Lusch, M. J. Tetrahedron 1982, 19, 2939.
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25. We thank Professor Ken Houk an Dr. Jim Na for supplying the coordinates of their published structures.
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