Four γ-diketones were synthesized by using a modification of the Kolbe electrolytic condensation of β-ketocarboxylic acids. [--see equation in thesis--] The following γ-diketones were synthesized in moderate yields: 2,5-hexanedione, 4,7-decanedione, 2,2,7,7-tetramethyl- 3,6-octanedione, and 1,4-diphenyl-1,4-butanedione (34, 39, 23, and 27, respectively). However, attempted preparation of the following γ-diketones failed: 3,4-dimethyl- 2,5-hexanedione, 3,3,4,4-tetramethyl-2,5-hexanedione, and 1,4-di(2-thienyl)-1,4-butanedione. Attempts to electrolytically condense α-alkyl and α, α-dialkyl substituted monocarboxylic acids have been reported and all attempts have ended in failure; similarly, the attempts to synthesize 3,4-dimethyl and 3,3,4,4-tetramethyl- 2,5-hexanedione from 2-methyl and 2,2-dimethyl-3- oxobutanoic acid, respectively, failed. The preparation of 1,4-di(2-thienyl)-l,4-butanedione failed because the product or side product was not soluble in the solvents tried and this resulted in precipitation of a non-conducting white product film on the electrodes, thus, preventing further electrolysis.
| Identifer | oai:union.ndltd.org:BGMYU2/oai:scholarsarchive.byu.edu:etd-9321 |
| Date | 01 May 1972 |
| Creators | Pahler, Leon F. |
| Publisher | BYU ScholarsArchive |
| Source Sets | Brigham Young University |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Theses and Dissertations |
| Rights | http://lib.byu.edu/about/copyright/ |
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