Intramolecular electrophilic aromatic substitution reactions with methyl vinyl ethers for the synthesis of dihydronaphthalenes
Intramolecular electrophilic aromatic substitution reactions with methyl vinyl ethers for the synthesis of dihydronaphthalenes
A simple and inexpensive method to effect the conversion of 4-arylalk-1-en-1-yl methyl ethers to dihydronaphthalenes has been developed. Cyclisation is accomplished by warming a toluene solution of the substrate with 1,2-ethanediol and para-toluenesulfonic acid and proceeds via in situ formation of a 1,3-dioxolane. Reactions generally give good yields and have been successful with electron rich, unsubstituted and halogenated arenes. They display excellent regioselectivity; appearing to follow the course of lowest steric demand.
oxidized metabolites
5971-5972
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Tyte, M. J.
4f091524-6ed0-49f5-baa4-34ea8b7bcf82
19 August 2002
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Tyte, M. J.
4f091524-6ed0-49f5-baa4-34ea8b7bcf82
Harrowven, D. C. and Tyte, M. J.
(2002)
Intramolecular electrophilic aromatic substitution reactions with methyl vinyl ethers for the synthesis of dihydronaphthalenes.
Tetrahedron Letters, 43 (34), .
(doi:10.1016/S0040-4039(02)01253-4).
Abstract
A simple and inexpensive method to effect the conversion of 4-arylalk-1-en-1-yl methyl ethers to dihydronaphthalenes has been developed. Cyclisation is accomplished by warming a toluene solution of the substrate with 1,2-ethanediol and para-toluenesulfonic acid and proceeds via in situ formation of a 1,3-dioxolane. Reactions generally give good yields and have been successful with electron rich, unsubstituted and halogenated arenes. They display excellent regioselectivity; appearing to follow the course of lowest steric demand.
This record has no associated files available for download.
More information
Published date: 19 August 2002
Keywords:
oxidized metabolites
Identifiers
Local EPrints ID: 19762
URI: http://eprints.soton.ac.uk/id/eprint/19762
ISSN: 0040-4039
PURE UUID: b987475d-e979-4dba-9a72-b92007427bff
Catalogue record
Date deposited: 20 Feb 2006
Last modified: 16 Mar 2024 02:46
Export record
Altmetrics
Contributors
Author:
M. J. Tyte
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
