Show simple item record

dc.contributor.authorTran, Richard
dc.date.accessioned2017-09-25 19:47:05 (GMT)
dc.date.available2018-01-24 05:50:06 (GMT)
dc.date.issued2017-09-25
dc.date.submitted2017
dc.identifier.urihttp://hdl.handle.net/10012/12451
dc.description.abstractFluorination chemistry is a branch of study that appeals to the pharmaceutical and agricultural industries. Drawbacks of popular methods of forming carbon-fluorine bonds include high cost or hazardous conditions that are often associated with some of these reagents. A less explored route to organofluorine substrates can be achieved through hypervalent iodine compounds, such as (difluoroiodo)toluene (TolIF2). There is large interest in these compounds because of their mild reactivity, relatively inexpensive production, and environmentally benign by-products. Previously disclosed by the Murphy group is the α-carbonyl difluorination of phenyldiazoacetate compounds using (difluoroiodo)toluene to furnish gem-difluorinated products. Detailed in this report is an extension of the work established by Murphy et al. in the synthesis of 3,3-difluoro-2-oxindole compounds starting from diazo oxindoles. Studies were also performed on tosylhydrazone, hydrazone and dithiane derivatives of oxindole. In addition, the fluorination protocol was used to synthesize N,N-dimethyl-p-nitrophenyldifluoroacetamide from its corresponding α-diazo amide. Finally, strategies towards the synthesis of other phenyldiazoacetamides are discussed in this thesis.en
dc.language.isoenen
dc.publisherUniversity of Waterlooen
dc.subjectOrganic chemistryen
dc.subjectfluorinationen
dc.subjectdiazoen
dc.subject(difluoro)iodotolueneen
dc.subjecthypervalent iodineen
dc.titleGem-Difluorination of α-Diazo Amides Using (Difluoroiodo)tolueneen
dc.typeMaster Thesisen
dc.pendingfalse
uws-etd.degree.departmentChemistryen
uws-etd.degree.disciplineChemistryen
uws-etd.degree.grantorUniversity of Waterlooen
uws-etd.degreeMaster of Scienceen
uws-etd.embargo.terms4 monthsen
uws.contributor.advisorMurphy, Graham
uws.contributor.affiliation1Faculty of Scienceen
uws.published.cityWaterlooen
uws.published.countryCanadaen
uws.published.provinceOntarioen
uws.typeOfResourceTexten
uws.peerReviewStatusUnrevieweden
uws.scholarLevelGraduateen


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record


UWSpace

University of Waterloo Library
200 University Avenue West
Waterloo, Ontario, Canada N2L 3G1
519 888 4883

All items in UWSpace are protected by copyright, with all rights reserved.

DSpace software

Service outages