DFT study on the mechanism of the cross Diels-Alder of monosulfonyl-1,3-dienes

سال انتشار: 1397
نوع سند: مقاله کنفرانسی
زبان: انگلیسی
مشاهده: 341

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شناسه ملی سند علمی:

IRANCC20_343

تاریخ نمایه سازی: 28 اردیبهشت 1398

چکیده مقاله:

Although the Diels-Alder dimerization reactions of conjugated dienes are frequently observed; the cross Diels-Alder (CDA) reactions between two different conjugateddienes have not been systematically studied [1]. The CDA reactions usually produce mixtures of all possible structural stereoisomeric and regioisomeric cycloadducts [2].The stereo- and regioselectivity of the CDA reactions can be controlled and only one of the products produced. Herein, the mechanistic details of these reactions, especially with respect to regio- and stereoselectivity, for the CDA reactions of 2- sulfonyl butadiene 1 with cylopentadiene 2 using the DFT method in the gas phase and in solvent were analyzed. Then, some possible cycloaddition reactions that are related to the participation of each reactant of 2π and 4π electrons were proposed. The calculated energy results indicated that the studied cycloaddition reactions proceed through concerted reaction mechanism with the most asynchronicity. Also, an analysis of the relative energies which were associated with the different reaction pathways showed that the monoulfone 1 in the most stable cycloaddition reactions is reacting as the dienophilic part with the vinyl group on the exo face. The steric and secondary orbital orientation overlapping is the reason of this direction. Moreover, analysis of the conceptual DFT reactivity indices allows the explanation of the reactivity, and the regioselectivity.

نویسندگان

Sepideh masoomifar

Department of Chemistry, Islamic Azad University, Babol branch, Babol, Iran, Iran

Mina Haghdadi,

Department of Chemistry, Islamic Azad University, Babol branch, Babol, Iran, Iran

Soheila Heidari Parastar

Department of Chemistry, Islamic Azad University, Babol branch, Babol, Iran, Iran

atieh marzban

Department of Chemistry, Islamic Azad University, Babol branch, Babol, Iran, Iran