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.

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