Alkylation of Benzene with Optically Active 3-Chloro-1-butanol, 3-Chlorobutanoic Acid, and Their Esters

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Abstract
The alkylations of benzene with optically active 3-chloro-1-butanol, 3-chlorobutanoic acid and their esters in the presence of aluminium chloride gave the corresponding 3-phenyl substituted derivatives in good optical yield. All these reactions were found to proceed with inversion of configuration at the attacking carbon atom. The products were not racemized under the conditions used, while the starting materials were racemized to a considerable extent during the reaction. Taking into account of the optical purity of the starting material recovered before the completion of reaction, net stereospecificity of each reaction was calculated to be about 90% except for the case of 3-chloro-1-butanol and its acetic ester. The high degree of stereospecificity of the reaction can be interpreted by the mechanism involving cyclic intermediate formed from the alkylating reagent and aluminium chloride.

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