Stereochemistry of Friedel-Crafts Reaction of Benzene with Optically Active 2-Methyloxetane

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Abstract
The Friedel-Crafts alkylation of benzene with (+)-2-methyloxetane in the presence of Lewis acids (AlCl3, SnCl4, and TiCl4) gave 3-phenyl-1-butanol with 20–60% inversion of configuration at the reaction center and a mixture of 4-chloro-2-butanol and 3-chloro-1-butanol in optically active form as the by-products. These by products were formed by the attack of the chlorine atom in Lewis acid. The stereochemical course of the reaction to 3-chloro-1-butanol varied with the kind of catalyst, i.e., inversion with AlCl3 or TiCl4 and retention with SnCl4. The addition of nitromethane to the reaction system promoted the retentive ring-opening to 3-chloro-1-butanol.