COUNTERATTACK REAGENT BIS(TRIMETHYLSILYL)ACETAMIDE IN THE DISILYLATION OF DIOLS

被引：11
|
作者：
HWU, JR
ANDERSON, DA
WANG, NL
BUCHNER, MM
GANI, P
TSAY, SC
机构：
[1] Department of Chemistry, Johns Hopkins University, Baltimore, Maryland
来源：
CHEMISCHE BERICHTE | 1990年 / 123卷 / 08期
关键词：
Bis(trimethylsilyl)acetamide; Counterattack reagent; Diol; Disilylation; Tandem double‐counterattack process;
D O I：
10.1002/cber.19901230815
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The counterattack method was applied to the disilylation of diols. Treatment of various diols with 0.3 or 1.1 equivalents of potassium hydride and 1.1 equivalents of bis(trimethylsilyl)‐acetamide in THF gave the corresponding disilyl ethers in good to excellent yields (60–95%). The diols may contain other functionalities, such as amide, amine, ether, and thioether. The diols used in the disilylation were 2a–14a. The newly developed disilylation proceeded in one flask by a sequential deprotonation‐silylation‐deprotonation‐silylation pathway. This disilylation also represents an example of a “tandem double‐counterattack process”. Bis(trimethylsilyl)‐acetamide acted as a counterattack reagent; it provided two Me3Si groups to diols and produced amides as bases. Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
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页码：1667 / 1671
页数：5
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