PREPARATION AND SOME REACTIONS OF ALLYLIC INDIUM REAGENTS

被引：105

作者：

ARAKI, S ^{[1
]}

SHIMIZU, T ^{[1
]}

JOHAR, PS ^{[1
]}

JIN, SJ ^{[1
]}

BUTSUGAN, Y ^{[1
]}

机构：

[1] NAGOYA INST TECHNOL,DEPT APPL CHEM,GOKISO CHO,SHOWA KU,NAGOYA,AICHI 466,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 07期

关键词：

D O I：

10.1021/jo00007a050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of allylic indium sesquihalides were readily prepared by the reaction of indium powder with allylic halides in DMF at room temperature. Protonation of the allylindium reagents proceeded regiospecifically at the gamma-position of the allylic group to give 1-propenes. A facile transformation of alpha-pinene to beta-pinene was achieved via a myrtenylindium intermediate. Oxygenation of the allylic indium reagents gave mixtures of allylic alcohol isomers in moderate yields. The coupling of the allylindium reagents with cyclic imides gave diverse products depending on the structures of the substrates and the reagents. Stannylation with tributylchlorostanane occurred exclusively at the alpha-carbon, yielding allytributylstannanes; E, Z isomerization of the allylic double bond depended largely upon the substitution pattern on the allylic moiety.

引用

页码：2538 / 2542

页数：5

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