2,1-Benzothiazines: preparation and reactivity

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2,1-Benzothiazines: preparation and reactivity

Please use this identifier to cite or link to this item: http://hdl.handle.net/10355/8309

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dc.contributor.advisor Harmata, Michael, 1959- en_US
dc.contributor.author Calkins, Nathan L., 1982- en_US
dc.date.accessioned 2010-08-23T16:43:06Z
dc.date.available 2010-08-23T16:43:06Z
dc.date.issued 2010 en_US
dc.date.submitted 2010 Spring en_US
dc.identifier.other CalkinsN-042210-D3359 en_US
dc.identifier.uri http://hdl.handle.net/10355/8309
dc.description Title from PDF of title page (University of Missouri--Columbia, viewed on May 24, 2010). en_US
dc.description The entire thesis text is included in the research.pdf file; the official abstract appears in the short.pdf file; a non-technical public abstract appears in the public.pdf file. en_US
dc.description Dissertation advisor: Dr. Michael Harmata. en_US
dc.description Vita. en_US
dc.description Includes bibliographical references. en_US
dc.description Ph. D. University of Missouri--Columbia 2010. en_US
dc.description Dissertations, Academic -- University of Missouri--Columbia -- Chemistry. en_US
dc.description.abstract The synthesis of chiral ligands to tune the reactivity and stereoselectivity of many catalytic asymmetric reactions has been given considerable attention in synthetic organic chemistry over the past decade. This report will show the results of efforts toward the syntheses of several families of enantiomerically pure 2,1-benzothiazine ligands. These ligands are unique in that they contain a chiral sulfoximine. Several 2,1-benzothiazine ligands were prepared in single one-pot syntheses and others in as many as five or more steps for larger heterocycles. An optimized synthetic route will be shown for a very well known Buchwald Hartwig N-arylation of sulfoximines and haloarenes. The synthetic procedure for the N-arylation of sulfoximines synthetic procedure has virtually been unchanged since its introduction in 1998. The new synthesis herein has dramatically improved reaction time and scope for the N-arylation of aryl bromides and aryl chlorides. Until now, aryl chloride based N-arylations gave extremely poor conversions when attempted thermally. Lastly, unsubstituted and 4-phenyl substituted 2,1-benzothiazine lithiation reactivity will be discussed for the sulfoximine stabilized lithium vinyl carbanions. Mono- and di-substitutions are now synthetically possible. New synthetic strategies for accessing the ortho-S-phenyl ring as a viable carbanion will also be shown. en_US
dc.format.extent xv, 273 pages en_US
dc.language.iso en_US en_US
dc.publisher University of Missouri--Columbia en_US
dc.relation.ispartof 2010 Freely available dissertations (MU) en_US
dc.subject.lcsh Benzothiazine en_US
dc.subject.lcsh Organic compounds -- Synthesis en_US
dc.subject.lcsh Sulfoximines en_US
dc.title 2,1-Benzothiazines: preparation and reactivity en_US
dc.type Thesis en_US
thesis.degree.discipline Chemistry en_US
thesis.degree.grantor University of Missouri--Columbia en_US
thesis.degree.name Ph. D. en_US
thesis.degree.level Doctoral en_US
dc.identifier.merlin b77789775 en_US
dc.identifier.merlin b77789775
dc.identifier.oclc 651669134 en_US
dc.relation.ispartofcommunity University of Missouri-Columbia. Graduate School. Theses and Dissertations. Dissertations. 2010 Dissertations


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