SYNTHETIC AND KINETIC-STUDIES OF SUBSTITUENT EFFECTS IN THE FURAN INTRAMOLECULAR DIELS-ALDER REACTION

被引：31

作者：

MCNELIS, BJ ^{[1
]}

STERNBACH, DD ^{[1
]}

MACPHAIL, AT ^{[1
]}

机构：

[1] DUKE UNIV,PAUL M GROSS CHEM LAB,DURHAM,NC 27706

来源：

TETRAHEDRON | 1994年 / 50卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(01)81331-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Intramolecular Diels-Alder reactions (IMDA) of a series of 2-sulfone substituted 1-furyl-4-penten-1-ols, 5a-c, have been studied. As the steric demands of the alkyl group on the sulfone was increased the rate and product yields in the IMDA reaction have also been observed to increase. The kinetics of these systems have been studied in detail as well as solvent effects to quantify substituent group effects in the cyclization reactions. Activated dienophiles (CO(2)Me) in these systems have been shown to be very reactive, cyclizing at ambient temperature.

引用

页码：6767 / 6782

页数：16

共 47 条

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