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Synthesis and photochemical reactions of 6-alkenyl-3-phenylcyclohex-2-enones |
Bradley, Stephen Anthony
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THESIS 7067 The synthesis and photochemical reactions of a series of molecules containing both the 3-phenylcylohexenone moiety and an C-6 substituted alkenyl side chain (2- propenyl, 3-butenyl and 4-pentenyl) are described. The C-6 position was further substituted with a carbomethoxy group to generate a conformational control factor.A synthetic strategy involving a three-step sequence was employed. This involved alkylation of a β-ketoester with a halogenated substituent, followed by Michael addition, with phenyl vinyl ketone prior to ring closure to the cyclohexenone. Cyclohexenone derivatives containing a pyrimidine ring were also investigated. In this case results suggested a thermodynamically controlled reaction with pka dependency in the Michael addition step.
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Keyword(s):
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Chemistry, Ph.D.; Ph.D. Trinity College Dublin |
Publication Date:
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2002 |
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Type:
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Doctoral thesis |
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Peer-Reviewed:
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Unknown |
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Language(s):
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English |
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Institution:
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Trinity College Dublin |
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Citation(s):
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Stephen Anthony Bradley, 'Synthesis and photochemical reactions of 6-alkenyl-3-phenylcyclohex-2-enones', [thesis], Trinity College (Dublin, Ireland). School of Chemistry, 2002, pp 253 |
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Publisher(s):
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Trinity College (Dublin, Ireland). School of Chemistry |
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Supervisor(s):
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Jeffares, Mark
McMurry, T. B. H. |
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First Indexed:
2019-05-16 06:12:34 Last Updated:
2020-07-28 08:26:21 |
