Date of Award
Master of Science (MS)
David H. Buchanan
The reaction of 4-amino-3-allyl-3-penten-2-one (7) with mercuric acetate in acetic acid was found to produce 4-amino-1-pentene (12) in 70% yield. The scope of this unusual cleavage reaction was investigated by systematic variation of substituents on the enamino ketone framework, the metal salt and the solvent. The presence of the allyl group was necessary for the reaction to produce compound 12.
Under a variety of conditions there was no evidence for cyclization of 7 to give heterocyclic compounds. Neither was there evidence for cyclization in reactions of 4-amino-3-penten-2-one with vinyl acetate in the presence of mercury (II) or thallium (III) salts as might have been expected from prior work.
Joshi, Suhas Satchidanand, "Metal Promoted Reactions of Enamino Ketones" (1974). Masters Theses. 3601.
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