A study of proposed intermediates in the deoxofluorination of carbonyl groups by SF4

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dc.contributor.authorStuart, Daniel
dc.contributor.authorUniversity of Lethbridge. Faculty of Arts and Science
dc.contributor.supervisorGerken, Michael
dc.date.accessioned2018-09-05T15:46:28Z
dc.date.available2018-09-05T15:46:28Z
dc.date.issued2018
dc.degree.levelMastersen_US
dc.description.abstractThe [SF4·O=C(CH3)2]2 and SF4·[O=C(CH3)2]2 adducts were synthesized and characterized at low temperature (LT) using Raman spectroscopy and, in the case of [SF4·O=C(CH3)2]2, single-crystal X-ray diffraction. The X-ray crystal structure of SF4·(O=C10H14)·(HF) was obtained, showing F4S---F−H---O=C10H14 interactions. Adducts of [SF3]+ with acetone, cyclopentanone, and 2-adamantanone were shown by 19F and 1H NMR spectroscopy to exist in solutions below −40 °C. The proposed [SF3·{O=C(CH3)2}3]+ cation was observed at LT by reacting [SF3][AsF6] with excess acetone. Above −40 °C SF4 formation was observed. Protonated ketones, [HO=R]+ (R = C(CH3)2, C5H8, C10H14), and aldehydes, [H(O=CHC6H5)2]+ and [H(O=CHCH3)x]+ (x = 1 or 2), were isolated and characterized in the solid state for the first time. NBO analyses were used to quantify the increase in electrophilicity of the oxonium cations. The AsF5·O=R (R = C(CH3)2, C5H8, C10H14) adducts were synthesized and characterized in solution and solid state using LT NMR and Raman spectroscopies, respectively.en_US
dc.embargoNoen_US
dc.identifier.urihttps://hdl.handle.net/10133/5195
dc.language.isoen_USen_US
dc.proquest.subject0485en_US
dc.proquest.subject0488en_US
dc.proquest.subject0494en_US
dc.proquestyesYesen_US
dc.publisherLethbridge, Alta. : Universtiy of Lethbridge, Department of Chemistry and Biochemistryen_US
dc.publisher.departmentDepartment of Chemistry and Biochemistryen_US
dc.publisher.facultyArts and Scienceen_US
dc.relation.ispartofseriesThesis (University of Lethbridge. Faculty of Arts and Science)en_US
dc.subjectOrganofluorine compoundsen_US
dc.subjectSulfur tetrafluorideen_US
dc.subjectCarbonyl compoundsen_US
dc.subjectLewis acidsen_US
dc.subjectdeoxofluorination reactionsen_US
dc.subjectLewis acid-base reactionsen_US
dc.subjectorganic carbonyl compoundsen_US
dc.subjectorganofluorine chemistryen_US
dc.titleA study of proposed intermediates in the deoxofluorination of carbonyl groups by SF4en_US
dc.typeThesisen_US
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