New organometallic approaches to heterocycles

dc.contributor.author Harrison, Leslie
dc.contributor.department Chemistry
dc.date 2018-08-16T16:03:14.000
dc.date.accessioned 2020-07-02T06:10:31Z
dc.date.available 2020-07-02T06:10:31Z
dc.date.copyright Sun Jan 01 00:00:00 UTC 1984
dc.date.issued 1984
dc.description.abstract <p>Several heterocyclic ring systems have been prepared by two new organometallic methods. The first approach involved the mercuration of alkyl aryl acetylenes. This reaction resulted in the formation of mercurated heterocycles. Mercurated benzofurans, isocoumarins, chromones, benzothiophenes and benzopyrans were all prepared by this method. The mercury moiety in these compounds was readily substituted by various functional groups. By making a slight modification in the acetylenic substrate, the intramolecular cyclization was prevented. The reaction then produced the (beta)-acetoxy vinylmercurial which was used to synthesize the coumarin ring system. The second approach involved the intramolecular attack of an oxygen or a nitrogen nucleophile on a (pi)-allylpalladium intermediate. The (pi)-allylpalladium intermediate was generated by the reaction of an organomercurial with a diene or an olefin in the presence of a palladium(II) salt. This method was used for the preparation of lactones, dihydrobenzofurans, dihydroindoles and pyrans.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/rtd/8993/
dc.identifier.articleid 9992
dc.identifier.contextkey 6347522
dc.identifier.doi https://doi.org/10.31274/rtd-180813-8948
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath rtd/8993
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/82042
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/rtd/8993/r_8423638.pdf|||Sat Jan 15 02:19:48 UTC 2022
dc.subject.disciplines Organic Chemistry
dc.subject.keywords Chemistry
dc.subject.keywords Chemistry
dc.subject.keywords Organic
dc.title New organometallic approaches to heterocycles
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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