Date of Award


Degree Type


Degree Name

Master of Science (MS)

Author's Department


First Advisor

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.

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Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.

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