Simon J. Coles
Bi(III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: An expeditious entry to tetralins
Coles, Simon J.; Costello, James F.; Draffin, William N.; Hursthouse, Michael B.; Paver, Simon P.
Authors
James Costello James.Costello@uwe.ac.uk
Senior Lecturer
William N. Draffin
Michael B. Hursthouse
Simon P. Paver
Abstract
The mild (DCM/20°C), quantitative, regioselective, O-acylative cleavage of tetrahydrofurans using organic acid halides with catalytic Bi(III) halides is reported. X-ray crystallography is used to rationalise the failure of the reaction in the case of certain crowded acid chlorides, and a useful aspect of chemoselectivity is revealed. The synthetic potential of this reaction is illustrated with a highly efficient O-acylative cleavage/intramolecular alkylation approach to tetralins. © 2005 Elsevier Ltd. All rights reserved.
Citation
Coles, S. J., Costello, J. F., Draffin, W. N., Hursthouse, M. B., & Paver, S. P. (2005). Bi(III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: An expeditious entry to tetralins. Tetrahedron, 61(18), 4447-4452. https://doi.org/10.1016/j.tet.2005.02.080
Journal Article Type | Article |
---|---|
Publication Date | May 2, 2005 |
Journal | Tetrahedron |
Print ISSN | 0040-4020 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 61 |
Issue | 18 |
Pages | 4447-4452 |
DOI | https://doi.org/10.1016/j.tet.2005.02.080 |
Keywords | O-acylative cleavage, ether, tetralins |
Public URL | https://uwe-repository.worktribe.com/output/1049759 |
Publisher URL | http://dx.doi.org/10.1016/j.tet.2005.02.080 |
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