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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
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
0040-4039
5971-5972
Harrowven, D. C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Tyte, M. J.
4f091524-6ed0-49f5-baa4-34ea8b7bcf82
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), 5971-5972. (doi:10.1016/S0040-4039(02)01253-4).

Record type: Article

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.

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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
ORCID for D. C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 20 Feb 2006
Last modified: 09 Jan 2022 02:46

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Contributors

Author: D. C. Harrowven ORCID iD
Author: M. J. Tyte

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