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  Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes

Fürstner, A., Kollegger, G., & Weidmann, H. (1991). Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes. Journal of Organometallic Chemisty, 414(3), 295-305. doi:10.1016/0022-328X(91)86327-M.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-000E-E68F-2 Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-5991-5
Genre: Journal Article

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 Creators:
Fürstner, Alois1, Author           
Kollegger, Gerlinde1, Author
Weidmann, Hans1, Author
Affiliations:
1Institute of Organic Chemistry, Technical University Graz, ou_persistent22              

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 Abstract: Trimethylsilylmethyl ketones, readily available from acyl chlorides, undergo a Reformatsky-Peterson reaction sequence to give 3-alkenoates regioselectively. Acylsilanes, however, react with either zinc ester enolates or trimethylsilylmethylmagnesium chloride to give the correspondmg tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement-Peterson olefination sequence. These reactions allow the selective formation of vinylsilanes.

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Language(s): eng - English
 Dates: 1991-02-211991-08-27
 Publication Status: Issued
 Pages: 11
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/0022-328X(91)86327-M
 Degree: -

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Title: Journal of Organometallic Chemisty
Source Genre: Journal
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Publ. Info: Lausanne : Elsevier Sequoia S.A.
Pages: 11 Volume / Issue: 414 (3) Sequence Number: - Start / End Page: 295 - 305 Identifier: ISSN: 0022-328X
DOI: 10.1016/0022-328X(91)86327-M