Harrowven, D. C. and Tyte, M. J.
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).
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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.
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