AB-INITIO STUDY OF THE THERMAL AND LEWIS ACID-CATALYZED HETERO-DIELS-ALDER REACTIONS OF 1,3-BUTADIENE AND ISOPRENE WITH SULFUR-DIOXIDE

被引：40

作者：

SUAREZ, D

GONZALEZ, J

SORDO, TL

SORDO, JA

机构：

[1] UNIV OVIEDO,FAC QUIM,DEPT QUIM FIS & ANALIT,E-33006 OVIEDO,SPAIN

[2] UNIV OVIEDO,INST QUIM ORGANOMET ENRIQUE MOLES,E-33006 OVIEDO,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 26期

关键词：

D O I：

10.1021/jo00105a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ab initio calculations at the MP2/6-31G*//RHF/6-31G* theory level provide data on the stereoselectivity and regioselectivity of the hetero Diels-Alder addition of sulfur dioxide to 1,3-butadiene and isoprene which are in good agreement with experimental evidence. Calculations indicate the importance of an electron-releasing methyl group in 1,3-butadiene (isoprene) as well as the remarkable role played by a Lewis acid catalyst. The existence of a CH-O electrostatic interaction is directly related to the stereoselectivity and regioselectivity of the cycloaddition.

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页码：8058 / 8064

页数：7

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