Cyclophanes from kinetically stabilized bis(isobenzofuran)s

dc.contributor.authorRobbins, Steven J.
dc.contributor.authorUniversity of Lethbridge. Faculty of Arts and Science
dc.contributor.supervisorDibble, Peter W.
dc.contributor.supervisorBoeré, René T.
dc.date.accessioned2009-10-13T15:45:49Z
dc.date.available2009-10-13T15:45:49Z
dc.date.issued2009
dc.degree.levelMasters
dc.descriptionxxii, 122 leaves : ill. ; 29 cm.en
dc.description.abstractIsobenzofurans (IBF)s are interesting molecules with regards to their structure and reactivity. The properties of these compounds are investigated through the use of gas phase calculations and kinetic studies. This work provides insight into the aromatic character of IBF and how substituents affect IBF’s reactivity. Substituted derivatives of naphtho[1,2-c:5,6-c]difuran are synthesized and reacted with tethered bis(dienophile)s to form cyclophanes. Phenyl-substituted naphtho[1,2-c5,6-c]difuran forms only a single isomer when reacted with a tethered bis(acrylate) and a tert-butyldimethylsilyl-substituted derivative exhibits higher selectivity towards cyclophane formation rather than polymer formation. Evidence for strong intramolecular interactions within these cyclophanes is presented as well. A five-step synthesis of anthra[1,2-c:7,8-c]difuran is developed, although with a poor overall yield. Similar reaction conditions could be applied to the synthesis of anthra[1,2-c:5,6-c]difuran. We also propose the synthesis of two different aromatic belts from these compounds.en
dc.identifier.urihttps://hdl.handle.net/10133/781
dc.language.isoen_USen
dc.publisherLethbridge, Alta. : University of Lethbridge, Deptartment of Chemistry and Biochemistry, 2009en
dc.publisher.departmentChemistry and Biochemistryen
dc.publisher.facultyArts and Scienceen
dc.relation.ispartofseriesThesis (University of Lethbridge. Faculty of Arts and Science)en
dc.subjectCyclophanes -- Synthesisen
dc.subjectDissertations, Academicen
dc.titleCyclophanes from kinetically stabilized bis(isobenzofuran)sen
dc.typeThesisen
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