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


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).

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Description/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.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1016/S0040-4039(02)01253-4
ISSNs: 0040-4039 (print)
Keywords: oxidized metabolites
Subjects:
ePrint ID: 19762
Date :
Date Event
19 August 2002Published
Date Deposited: 20 Feb 2006
Last Modified: 16 Apr 2017 23:01
Further Information:Google Scholar
URI: http://eprints.soton.ac.uk/id/eprint/19762

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