Regioselectivity in the Diels-Alder reaction of 8,8-dimethylnaphthalene-1,4,5(8H)-trione with 2,4-hexadien-1-ol

被引：28

作者：

Araya-Maturana, R ^{[1
]}

Cassels, BK

Delgado-Castro, T

Valderrama, JA

Weiss-López, BE

机构：

[1] Univ Chile, Fac Ciencias Quim & Farmaceut, Dept Quim Organ & Fisicoquim, Santiago, Chile

[2] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

[3] Pontificia Univ Catolica Chile, Fac Quim, Santiago, Chile

来源：

TETRAHEDRON | 1999年 / 55卷 / 03期

关键词：

Diels-Alder reactions; quinones; regiocontrol; hydrogen bonding;

D O I：

10.1016/S0040-4020(98)01083-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reactions of 8,8-dimethylnaphtalene-1,4,5(8H)-trione with 2,4-hexadien-1-ol and its O-acetyl derivative were investigated in different solvents. The regiochemistry of the cycloaddition of the hexadienol was determined through chemical correlation of one of the products. The solvent effect on the regioselectivity and endo/exo selectivity of this reaction is attributed to intermolecular hydrogen bonding between the hydroxyl group of the diene and the carbonyl oxygen atoms at C-4 and C-5 of the quinone in the transition state. The possible transition states have been modelled by AMI calculations in order to better interpret these experimental results. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：637 / 648

页数：12

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