Abstract
The reaction mechanism and regioselectivity of cyclohex-3-en-1-yl ethanone derivatives synthesized by a Di- els-Alder reaction between 2-substituted 1,3-diene derivatives and but-3-en-2-one, were studied using density functional theory. Four possible reaction channels, which are related to the formation of meta cyclohex-3 en-1-yl ethanone and para cyclohex-3 en-1-yl ethanone, are investigated using natural bond orbital analysis, geometrical parameter analysis, energy analysis and frontier molecular orbital (FMO) analysis. The energy analysis shows that the larger activation energy prevents the formation of meta products, therefore para products are formed as the energetically favored product. The presence of a Lewis acid catalyst coordinated to the acyl oxygen atom markedly decreases the activation energy associated with the nucleophilic attack. The natural bond order analysis shows the reaction follows an asynchronous concerted mechanism.
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