Stereochemistry of Friedel-Crafts reaction of benzene with optically active 2-methyloxetane.
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概要
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The Friedel-Crafts alkylation of benzene with (+)-2-methyloxetane in the presence of Lewis acids (AlCl<SUB>3</SUB>, SnCl<SUB>4</SUB>, and TiCl<SUB>4</SUB>) 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>i.e.</I>, inversion with AlCl<SUB>3</SUB> or TiCl<SUB>4</SUB> and retention with SnCl<SUB>4</SUB>. The addition of nitromethane to the reaction system promoted the retentive ring-opening to 3-chloro-1-butanol.
- 公益社団法人 日本化学会の論文
著者
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Nakajima Tadashi
Department Of Applied Biology Faculty Of Textile Science And Technology Shinshu University
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Suga Sohei
Department of Industrial Chemistry, Faculty of Technology, Kanazawa University
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Segi Masahito
Department of Industrial Chemistry, Faculty of Technology, Kanazawa University
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Masuda Shinji
Ashikaga Institute of Technology
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Takebe Masaki
Department of Industrial Chemistry, Faculty of Technology, Kanazawa University
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Nakajima Tadashi
Department of Industrial Chemistry, Faculty of Technology, Kanazawa University
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