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Electrophilic Reactions of Silyl Enol Ethers

  • Chapter
Silicon Reagents for Organic Synthesis

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 14))

Abstract

The electron rich C-C double bond of silyl enol ethers is extremely susceptible to attack by electrophiles. Electrophiles regiospecifically attack the C-C double bond of trimethylsilyl enol ethers to yield a trimethylsilyloxy stabilized carbocation. Usually, the nucleophilic anion associated with the electrophile attacks the silyl center of this intermediate to yield a substituted ketone in which the electrophile is bonded to the α position.

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  1. Department of Chemistry, University of Southern California, 90007, University Park, Los Angeles, CA, USA

    William P. Weber

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  1. William P. Weber
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© 1983 Springer-Verlag Berlin Heidelberg

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Weber, W.P. (1983). Electrophilic Reactions of Silyl Enol Ethers. In: Silicon Reagents for Organic Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68661-0_12

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  • DOI: https://doi.org/10.1007/978-3-642-68661-0_12

  • Publisher Name: Springer, Berlin, Heidelberg

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