Synthesis of heterocycles via organopalladium intermediates

dc.contributor.author Liu, Chih-Ling
dc.contributor.department Chemistry
dc.date 2018-08-15T20:01:52.000
dc.date.accessioned 2020-07-02T06:07:19Z
dc.date.available 2020-07-02T06:07:19Z
dc.date.copyright Sat Jan 01 00:00:00 UTC 1983
dc.date.issued 1983
dc.description.abstract <p>A number of oxygen- and nitrogen-containing heterocycles have been prepared by employing organopalladium intermediates. First, mercuric chloride readily adds to the carbon-carbon triple bond of certain 4-hydroxy-2-alkyn-1-ones to give vinylmercurials which appear to be the first syn addition compounds of mercuric chloride. These vinylmercurials readily dehydrate to 3-furylmercurials. Palladium-promoted carbonylation of these compounds affords 3-furyl carbonyl compounds. Second, the mercuration of allenic acids and esters has been examined. Low yields of (beta)-substituted (DELTA)('(alpha),(beta))-butenolides could be obtained from mercuration and palladium-assisted carbonylation or acetoxylation of the allenic acid. Third, a new approach to the synthesis of tetracyclic sequiterpenes via vinylation-carbonylation of 2,3-dimethylnorbornadiene-palladium dichloride and 2-methylnorbornadiene-palladium dichloride was explored. Finally, palladium-assisted olefination-cyclization of thallated p-tolylacetic acid, N-methylbenzamide, benzamide, and acetanilide have been studied. N-Methylisoquinolones, isocarbostyrils, and indoles have been prepared by this new route in moderate to good yields. Our method, which employs organometallic intermediates, is often shorter and more efficient than older methods for obtaining many of the compounds studied.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/rtd/8500/
dc.identifier.articleid 9499
dc.identifier.contextkey 6335138
dc.identifier.doi https://doi.org/10.31274/rtd-180813-8593
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath rtd/8500
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/81496
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/rtd/8500/r_8407099.pdf|||Sat Jan 15 02:12:49 UTC 2022
dc.subject.disciplines Organic Chemistry
dc.subject.keywords Chemistry
dc.subject.keywords Chemistry
dc.subject.keywords Organic
dc.title Synthesis of heterocycles via organopalladium intermediates
dc.type article
dc.type.genre dissertation
dspace.entity.type Publication
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
thesis.degree.level dissertation
thesis.degree.name Doctor of Philosophy
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