Abstract
Abstract The Friedel-Crafts reaction of toluene and anisole with 2-methyloxirane and 2,3-dimethyloxiranes was examined. The inter- and intramolecular selectivities of 2-methyloxirane were between those of conventional methylation and isopropylation. It was also found that all the positional isomers formed by the aluminum chloridecatalyzed reaction of toluene and anisole had almost completely inverted configurations of the epoxide carbons. These results are explained by a mechanism of the SN2 type. Diminished stereospecificities were observed in aluminum bromide-catalyzed reactions.
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