DIELS-ALDER ADDUCTS FROM REACTIVE ARYL ACETOXY DIENES AND THE EFFECT OF STEREOCHEMISTRY ON THEIR CYCLOACYLATIONS

被引：3

作者：

BAYLOUNY, RA

DANNA, RP

TOTH, KH

机构：

[1] Chemistry Department, Fairieigh Dickinson University, Fiorham-Madison Campus, New Jersey, Madison

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 02期

关键词：

D O I：

10.1021/jo01316a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The interaction of aryl butenones with maleic and citraconic anhydride in the presence of isopropenyl acetate under acid conditions yielded Diels-Alder normal adducts (4a, 4b, 6) in 41-70% yields. When mesaconic acid was used, a 25% yield of trans 1,2-anhydride (8b) was realized. Friedel-Crafts cycloacylation of the cis anhydrides yielded bicyclo[3.3.l]nonanone ring systems (18, 19), whereas the trans anhydride produced substituted hydrofluore-nones (20,21). These observations are interpreted in terms of stereochemistry of cis and trans anhydrides. Copyright © 1979, American Chemical Society. All rights reserved.

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页码：204 / 209

页数：6

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