Effect of Boron Trifluoride on the Transesterification of Boronate Esters

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dc.contributor.advisorGross, Dustin E.
dc.creatorEkanayake, Dulamini
dc.date.accessioned2019-08-15T14:49:01Z
dc.date.available2019-08-15T14:49:01Z
dc.date.created2017-08
dc.date.issued2017-06-29
dc.date.submittedAugust 2017
dc.date.updated2019-08-15T14:49:01Z
dc.description.abstractBoronate ester-based materials have received interest and found utility in many applications. The preeminent goal of this research is to advance the field of boron-oxygen based porous materials. The formation of these materials has been predominantly facilitated by boron-oxygen dynamic covalent character. In an effort to understand and improve this process, we are investigating the effect of boron trifluoride, a well-known Lewis acid catalyst, on synthesis and exchange of dioxaboroles. From our previous studies, we have observed an increase in reaction rate as well as beneficial side reactions, which have driven the reaction equilibrium to unexpected products from the transesterification of phenyl pinacol boronate ester (PPB) in the presence of boron trifluoride. Initially, we studied the effect of boron trifluoride on the transesterification of different boronate esters (dioxaboroles) with catechol. Then, we synthesized bis boronate ester materials by combining the knowledge learned in the above-described work. Finally, we investigated the Lewis acid-catalyzed (boron trifluoride and para-toluene sulfonic acid) pinacol rearrangement of different diols (pinacol, hydrobenzoin, and benzpinacol). In the presence of boron trifluoride all transesterification reactions of boronate esters with catechol showed an improvement. Additionally, we were able to find a method to isolate catechol boronate ester on the gram scale.
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/20.500.11875/2668
dc.language.isoen
dc.subjectBoronate esters
dc.subjecttransesterification
dc.subjectboron trifluoride
dc.subjectpinacol rearrangement
dc.titleEffect of Boron Trifluoride on the Transesterification of Boronate Esters
dc.typeThesis
dc.type.materialtext
thesis.degree.departmentChemistry
thesis.degree.grantorSam Houston State University
thesis.degree.levelMasters
thesis.degree.nameMaster of Science

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