Friedel-Crafts Reaction of Aromatics with Epoxides. Stereochemistry and Selectivities

Article abstract of DOI:10.1246/bcsj.53.458

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 aluminium chloride-catalyzed reaction of toluene and anisole had almost completely inverted configurations of the epoxide carbons.These results are explained by a mechanism of the S_N2 type.Diminished stereospecifities were observed in aluminium bromide-catalyzed reactions.