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Intramolecular electrophilic aromatic substitution reactions with methyl vinyl ethers for the synthesis of dihydronaphthalenes

Record type: Article

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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Citation

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), pp. 5971-5972. (doi:10.1016/S0040-4039(02)01253-4).

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: 17 Jul 2017 16:30

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Contributors

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

University divisions


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