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Synthesis and photochemical reactions of 6-alkenyl-3-phenylcyclohex-2-enones
Bradley, Stephen Anthony
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 ?-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.
Keyword(s): Chemistry, Ph.D.; Ph.D. Trinity College Dublin
Publication Date:
Type: Doctoral thesis
Peer-Reviewed: Unknown
Language(s): English
Institution: Trinity College Dublin
Citation(s): 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
Publisher(s): Trinity College (Dublin, Ireland). School of Chemistry
Supervisor(s): Jeffares, Mark
McMurry, T. B. H.
First Indexed: 2019-05-16 06:12:34 Last Updated: 2020-10-30 08:15:36