Abstract

The Friedel–Crafts alkylation of benzene with cyclohex-4-ene-1,2-dicarboxylic acid is studied by quantum chemical methods. Parameters of the starting compounds, products, and transition compounds are calculated by density functional theory (DFT) and ab initio Hartree–Fock (HF) methods. Theoretical enthalpies of formation show that it is more favorable for (1R,2S,4R)-4-phenylcyclohexane-1,2-dicarboxylic acid (syn-product) than for (1R,2S,4S)-4-phenylcyclohexane-1,2-dicarboxylic acid (anti-product). The data obtained are confirmed by HELC and ¹H-¹H NOESY spectroscopy. According the to results of the quantum chemical study and the experiment, the Friedel–Crafts alkylation of benzene with cyclohex-4-ene-1,2-dicarboxylic acid and subsequent modifications of the product are regio- and stereoselective.

中文翻译：

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苯与环己-4-烯-1,2-二甲酸烷基化反应的量子化学研究

摘要

采用量子化学方法研究了苯与环己-4-烯-1,2-二甲酸的弗里德尔-克来福特烷基化反应。起始化合物、产物和过渡化合物的参数通过密度泛函理论 (DFT) 和从头算Hartree-Fock (HF) 方法计算。理论生成焓表明 (1 R ,2 S ,4 R )-4-苯基环己烷-1,2-二甲酸（顺式产物）比 (1 R ,2 S ,4 S )-更有利4-苯基环己烷-1,2-二甲酸（反产物）。获得的数据经 HELC 和¹ H- ^1确认H NOESY 光谱。根据量子化学研究和实验的结果，苯与环己-4-烯-1,2-二甲酸的弗里德尔-克来福特烷基化以及随后的产物修饰具有区域和立体选择性。