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dc.contributor.advisorLee, Daesungen_US
dc.contributor.authorLiu, Huaqingen_US
dc.date.accessioned2014-06-20T17:12:24Z
dc.date.available2014-06-20T17:12:24Z
dc.date.created2014-05en_US
dc.date.issued2014-06-20
dc.date.submitted2014-05en_US
dc.identifier.urihttp://hdl.handle.net/10027/18797
dc.description.abstractThis thesis describes novel applications of trimethylsilyldiazomethane (TMSD) in synthetic organic chemistry. Part I of this work focuses on the methodology of cyclic ketone monomethylene homologation utilizing lithiated trimethylsilyldiazomethane. Subsequently, this methodology was further optimized to a more practical operation using neutral trimethylsilyldiazomethane catalyzed by the Lewis base tributylammonium triphenylsilyl difluorosilicate (TBAT) or potassium tert-butoxide. In part II of the thesis, the application of trimethylsilyldiazomethane as a C–N–N synthon in the 1,3-dipolar cycloaddition reactions is thoroughly reviewed. Then is described a novel process whereby the sequential reaction of trimethylsilyldiazomethane with 4-alkenyl ketones and aldehydes are catalyzed by Lewis bases, to form fused Δ1- and Δ2-pyrazolines. In part III of this thesis, yet another major application of trimethylsilyldiazomethane: generating alkylidene carbenes is reviewed, along with the reactions of these carbenes. Finally, is presented a novel alkylidene carbene chemistry whereby an olefin insertion/dimerization via a concerted [2 + 2] cycloaddition or involving trimethylenemethane (TMM) diradicals formed complex hydrocarbons.en_US
dc.language.isoenen_US
dc.rightsen_US
dc.rightsCopyright 2014 Huaqing Liuen_US
dc.subjecttrimethylsilyldiazomethaneen_US
dc.subjecthomologationen_US
dc.subjectcycloadditionen_US
dc.subjectpyrazolinesen_US
dc.subjectalkylidene carbeneen_US
dc.subjecttrimethylenemethane.en_US
dc.titleApplications of Trimethylsilyldiazomethane in Synthetic Organic Chemistryen_US
thesis.degree.departmentChemistryen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Illinois at Chicagoen_US
thesis.degree.levelDoctoralen_US
thesis.degree.namePhD, Doctor of Philosophyen_US
dc.type.genrethesisen_US
dc.contributor.committeeMemberGevorgyan, Vladimiren_US
dc.contributor.committeeMemberMohr, Justinen_US
dc.contributor.committeeMemberWardrop, Duncanen_US
dc.contributor.committeeMemberGomtsyan, Arthuren_US
dc.type.materialtexten_US


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