ISSN:
0009-2940
Keywords:
Counterattack reagent
;
Tandem double-counterattack process
;
Disilylation
;
Diol
;
Bis(trimethylsilyl)acetamide
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230815
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