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dc.contributor.advisorHarmata, Michaeleng
dc.contributor.authorTata, Rama Raoeng
dc.date.issued2015eng
dc.date.submitted2015 Summereng
dc.description.abstract[ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT REQUEST OF AUTHOR.] The scope of [2,3]-sigmatropic rearrangement of propargylic sulfinates to allenic sulfones by silver catalysis was expanded. A series of new propargylic sulfinate esters was generated from a variety of aromatic and heteroaromatic sulfonyl chlorides and their rearrangement to allenic sulfones is reported. In addition, the synthesis of propargylic sulfinate esters containing electron-withdrawing benzenesulfonyl chlorides was optimized and reported. In the course of pursuing a Nazarov cyclization of allenyl vinyl ketones (AVK), we discovered multiple new reactions. Allenyl alcohols underwent an intramolecular cyclization to 2,5-dihydrofurans in the presence of Fetizon's reagent and this process was then optimized using silver fluoride. The methodology was expanded to synthesize higher membered oxacycles also. A tandem cyclization of hydroxypropargylic sulfinate esters to 2,5-hydrofurans was also developed. A new synthesis of a'-hydroxyenones was developed by the oxidation of a-allenyl alcohols with Cr (VI) regents and then extended to synthesize dihydrofuran- 3(2H)-ones by acid catalysis.eng
dc.identifier.urihttps://hdl.handle.net/10355/50142
dc.languageEnglisheng
dc.publisherUniversity of Missouri--Columbiaeng
dc.relation.ispartofcommunityUniversity of Missouri--Columbia. Graduate School. Theses and Dissertationseng
dc.rightsAccess is limited to the campuses of the University of Missouri.eng
dc.titleThe [2,3]-sigmatropic rearrangement of propargylic sulfonates to allenic sulfones and further applications to oxacycles and dihydrofuranoneseng
dc.typeThesiseng
thesis.degree.disciplineChemistry (MU)eng
thesis.degree.grantorUniversity of Missouri--Columbiaeng
thesis.degree.levelDoctoraleng
thesis.degree.namePh. D.eng


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