Bi(III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: an expeditious entry to tetralins
Bi(III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: an expeditious entry to tetralins
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.
o-acylative cleavage, ether, tetralins, friedel-crafts intermediate, cyclic ethers, antimony pentachloride, molecular structure, addition-compounds, toluyl chlorides, acetic-anhydride, acid-chlorides, crystal, complexes
4447-4452
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Costello, James F.
c016b700-337d-4d5a-9d04-e05100f20e10
Draffin, William N.
083e9a15-5a12-4ce4-ad88-08f123c173ee
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Paver, Simon P.
28633373-4ec0-48f9-89b1-5a2a97e7fe86
2 May 2005
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Costello, James F.
c016b700-337d-4d5a-9d04-e05100f20e10
Draffin, William N.
083e9a15-5a12-4ce4-ad88-08f123c173ee
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Paver, Simon P.
28633373-4ec0-48f9-89b1-5a2a97e7fe86
Coles, Simon J., Costello, James F., Draffin, William N., Hursthouse, Michael B. and Paver, Simon P.
(2005)
Bi(III) halides as efficient catalysts for the O-acylative cleavage of tetrahydrofurans: an expeditious entry to tetralins.
Tetrahedron, 61 (18), .
(doi:10.1016/j.tet.2005.02.080).
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.
This record has no associated files available for download.
More information
Published date: 2 May 2005
Keywords:
o-acylative cleavage, ether, tetralins, friedel-crafts intermediate, cyclic ethers, antimony pentachloride, molecular structure, addition-compounds, toluyl chlorides, acetic-anhydride, acid-chlorides, crystal, complexes
Identifiers
Local EPrints ID: 20761
URI: http://eprints.soton.ac.uk/id/eprint/20761
ISSN: 0040-4020
PURE UUID: ec0a4542-35fb-4790-9fc5-7d47a15f812f
Catalogue record
Date deposited: 03 Mar 2006
Last modified: 16 Mar 2024 03:05
Export record
Altmetrics
Contributors
Author:
James F. Costello
Author:
William N. Draffin
Author:
Simon P. Paver
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
