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A facile synthesis of symmetrical 1,1-disubstituted ethylenes

✍ Scribed by Gerald L. Larson; David Hernández

Book ID
104220514
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
201 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reaction of ethyl trimethylsilylacetate with two equivalents of a Grignard reagent in ether followed by treatment with acid gives 1,1-disubstituted ethylenes in excellent yield. The use ofghydroxysilanes in the formation of olefins has been a useful reaction in organic chemistry since the first report of dehydroxysilylation by Peterson.2 Since that time numerous entries into !3-hydroxysilanes, and therefore olefins, have been reported.3 Surprisingly, the reaction of a-silylated esters with Grignard reagents has not been exploited in this regard.4

We wish to report herein on the reaction of ethyl trimethylsilylacetate,5 ,J,, with Grignard reagents to give, after acid treatment, the expected 1,1-disubstituted ethylenes, $,6 (eq. 11.

The results are shown in Table I.

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