A free radical synthesis of Y-lactones using tri-n-butylstannyl iodoesters

dc.contributor.author Landgrebe, Kevin
dc.contributor.department Chemistry
dc.date 2018-08-16T19:40:10.000
dc.date.accessioned 2020-07-02T06:08:44Z
dc.date.available 2020-07-02T06:08:44Z
dc.date.copyright Tue Jan 01 00:00:00 UTC 1985
dc.date.issued 1985
dc.description.abstract <p>Interest in the use of free radical reactions in synthetic organic chemistry has greatly intensified in recent years. A program was undertaken to develop a free radical synthesis of (gamma)-lactones which would occur under neutral conditions. Thus, treatment of olefins with tri-n-butylstannyl iodoacetate in the presence of a catalytic amount of the free radical initiator, 2,2'-azobis(2-methylpropionitrile) (AIBN) in refluxing benzene resulted in good yields of 4-substituted-(gamma)-lactones. The products were separated from iodotri-n-butylstannane by partitioning between acetonitrile and hexanes. Further purification by column chromatography afforded the pure (gamma)-lactones;This reaction has also been extended to the synthesis of bicyclic lactones via the intramolecular cyclizations of appropriately constructed tri-n-butylstannyl iodoesters under the same reaction conditions. The mild reaction conditions employed allow for the introduction of a variety of functional groups at the 4-position including alcohols, ethers, and even alkylsilanes and silyl ethers.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/rtd/8717/
dc.identifier.articleid 9716
dc.identifier.contextkey 6343473
dc.identifier.doi https://doi.org/10.31274/rtd-180813-8698
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath rtd/8717
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/81736
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/rtd/8717/r_8604487.pdf|||Sat Jan 15 02:16:02 UTC 2022
dc.subject.disciplines Organic Chemistry
dc.subject.keywords Chemistry
dc.subject.keywords Organic chemistry
dc.title A free radical synthesis of Y-lactones using tri-n-butylstannyl iodoesters
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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