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.
| Identifer | oai:union.ndltd.org:BGMYU2/oai:scholarsarchive.byu.edu:etd-9362 |
| Date | 01 June 1970 |
| Creators | Sudweeks, Walter Bentley |
| Publisher | BYU ScholarsArchive |
| Source Sets | Brigham Young University |
| Detected Language | English |
| Type | text |
| Source | Theses and Dissertations |
| Rights | http://lib.byu.edu/about/copyright/ |
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