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Generalized synthesis of [Gamma]-diketones

Various synthetic schemes were explored in order to develop a general synthesis of γ-diketones. The addition of organometallic reagents to several γ-dicarboxylic acids and γ-dinitrile compounds failed to produce any ketonic product, whereas addition to γ-diesters and γ-diacid chlorides gave only small amounts of the diketones in a mixture of products. A series of γ-diketones was prepared in low to moderate yields by way of the corresponding acetylenic glycols. These glycols were made by treating acetylenedimagnesium bromide with various aldehydes and then hydrogenation to the saturated γ-dialcohols. Oxidation of the alcohols produced diketones of type RCOCH_2CH_2COR where R = ethyl, isopropyl, t-butyl, n-propyl, n-hexyl, phenyl and cyclohexyl radicals. Good yields of γ-diketones were obtained by dialkylating 2,2'-ethylenebis(m-dithiane) followed by hydrolysis. Except for isopropyl iodide, the alkylation was successful only with primary alkyl halides. Diketones of the above type where R = ethyl, isopropyl, n-propyl, isobutyl, n-butyl, isoamyl, and benzyl radicals were prepared.

Identiferoai:union.ndltd.org:BGMYU2/oai:scholarsarchive.byu.edu:etd-9362
Date01 June 1970
CreatorsSudweeks, Walter Bentley
PublisherBYU ScholarsArchive
Source SetsBrigham Young University
Detected LanguageEnglish
Typetext
SourceTheses and Dissertations
Rightshttp://lib.byu.edu/about/copyright/

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