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Cyclophanes from kinetically stabilized bis(isobenzofuran)s

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dc.contributor.advisor Dibble, Peter
dc.contributor.advisor Boeré, René
dc.contributor.author Robbins, Steven Joseph
dc.contributor.author University of Lethbridge. Faculty of Arts and Science
dc.date.accessioned 2009-10-13T15:45:49Z
dc.date.available 2009-10-13T15:45:49Z
dc.date.issued 2009
dc.identifier.uri http://hdl.handle.net/10133/781
dc.description xxii, 122 leaves : ill. ; 29 cm. en
dc.description.abstract Isobenzofurans (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.language.iso en_US en
dc.publisher Lethbridge, Alta. : University of Lethbridge, Deptartment of Chemistry and Biochemistry, 2009 en
dc.relation.ispartofseries Thesis (University of Lethbridge. Faculty of Arts and Science) en
dc.subject Cyclophanes -- Synthesis en
dc.subject Dissertations, Academic en
dc.subject Electronic dissertations en
dc.title Cyclophanes from kinetically stabilized bis(isobenzofuran)s en
dc.type Thesis en
dc.publisher.faculty Arts and Science en
dc.publisher.department Chemistry and Biochemistry en

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