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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
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
0040-4020
4447-4452
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Costello, James F.
c016b700-337d-4d5a-9d04-e05100f20e10
Draffin, William N.
083e9a15-5a12-4ce4-ad88-08f123c173ee
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Paver, Simon P.
28633373-4ec0-48f9-89b1-5a2a97e7fe86
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Costello, James F.
c016b700-337d-4d5a-9d04-e05100f20e10
Draffin, William N.
083e9a15-5a12-4ce4-ad88-08f123c173ee
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
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), 4447-4452. (doi:10.1016/j.tet.2005.02.080).

Record type: Article

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.

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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: 15 Jul 2019 19:25

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