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), 5971-5972. (doi:10.1016/S0040-4039(02)01253-4).
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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.
|Digital Object Identifier (DOI):||doi:10.1016/S0040-4039(02)01253-4|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|Date Deposited:||20 Feb 2006|
|Last Modified:||06 Aug 2015 02:19|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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