Friedel-Crafts reaction of aromatics with epoxides. Stereochemistry and selectivities.
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概要
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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 <I>S</I><SUB>N</SUB>2 type. Diminished stereospecificities were observed in aluminum bromide-catalyzed reactions.
- 公益社団法人 日本化学会の論文
著者
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Inoue Masashi
Department Of Applied Physics Fukui University
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Sugita Toshio
Department Of Electrical Engineering Science University Of Tokyo
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Ichikawa Katsuhiko
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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Itoh Osamu
Department of Chemistry, The University of Tsukuba
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Chano Keizo
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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