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KMID : 1059519900340030248
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Journal of the Korean Chemical Society
1990 Volume.34 No. 3 p.248 ~ p.254
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Theoretical Studies on Electrophilic Substitution of Five-membered Heteroaromatic Compounds with Isopropyl Cation
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Lee Ik-Choon
Kim Chang Kon
Lee Bon-Su
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Abstract
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Theoretical studies on the electrophilic substitution reactions of five-membered heteroaromatic compounds, furan, pyrrole and thiophene, with isopropyl cation were carried out using the MNDO method. The results indicated that site selectivities of α,β and hetero-atoms are not controlled by electrostatic interactions but are determined mainly by charge trasfer stabilization between the HOMO of heteroaromatics and the LUMO of the electrophile. The reactivity order for αandβ positions was pyrrole > furan > thiophene, in agreement with the solution-phase as well as the gas-phase experimental results.
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