DIELS-ALDER REACTIONS OF 5,8-ETHANO-5,8-DIHYDRO-1,4-NAPHTHOQUINONE WITH CYCLIC DIENES

被引：3

作者：

CHOU, TC ^{[1
]}

LIOU, JA ^{[1
]}

LIN, CT ^{[1
]}

机构：

[1] TUNGHAI UNIV,DEPT CHEM,TAICHUNG 407,TAIWAN

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 1994年 / 41卷 / 05期

关键词：

POLYCYCLIC COMPOUNDS; DIHYDROETHANO-1,4-NAPHTHOQUINONE; DIELS-ALDER REACTION; PI-FACIAL SELECTIVITY; 1,4-CYCLOHEXADIONES;

D O I：

10.1002/jccs.199400075

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diels-Alder cycloadditions of 1,3-cyclohexadiene and cyclopentadiene to pi-facially dissymmetric 5,8-ethano-5,8-dihydro-1,4-naphthoquinone (1) were examined. The stereochemical outcome of the reactions, determined by a combination of chemical and spectral methods, indicates that addition of cyclic dienes to 1 occurs preferentially at the face syn to the etheno-bridge of 1. Cycloadducts 7a/7b and 8a/8b obtained from Diels-Alder reactions of 1 with cyclopentadiene and 1,3-cyclohexadiene undergo [2+2]-photocyclization to give caged compounds 9a/9b and 10a/10b, respectively. Stereoselective reduction of the enedione double bond in 7a/7b and 8a/8b with aqueous TiCl3, in acetone affords cis-bis-bicyclic ring-fused 1,4-cyclohexadiones 11a/11b, and 12a/12b, respectively.

引用

页码：565 / 572

页数：8

共 35 条

[1]

Alder K, 1933, LIEBIGS ANN CHEM, V501, P247

[2] Examinations into the process of diene synthesis. [J].