CLAISEN REARRANGEMENT OF ALLYL ETHYL KETENE ACETALS GENERATED INSITU VIA BENZENESELENENIC ACID ELIMINATION

被引：33

作者：

PITTELOUD, R

PETRZILKA, M

机构：

[1] Départment de Chimie Organique, Universitè de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 04期

关键词：

D O I：

10.1002/hlca.19790620445

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Mixed acetals 7 of benzeneseleninylacetaldehyde, prepared by a simple 2‐step procedure from mono‐ and bicyclic allylic alcohols 5, undergo benzeneselenenic acid elimination to transient ketene acetals 8 which afford γ, δ‐unsaturated esters 9 via the ester Claisen rearrangement Scheme 2. Under the same conditions selenoxide 7h derived from benzyl alcohol 5h is converted back to benzyl alcohol with the concomitant formation of ethylphenylselenoacetate 12. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1319 / 1325

页数：7

共 23 条

[11] NEW TYPE OF CLAISEN REARRANGEMENT INVOLVING 1,3-DIPOLAR INTERMEDIATES - PRELIMINARY COMMUNICATION [J].