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Novel bis(isobenzofuran)s and their utility in the synthesis of cyclophanes

The synthesis of 1,2-bis(5-isobenzofuranyl)ethene by two routes is described. The first route involved generation of 1,2-bis(5-isobenzofuranyl)ethene from a bis(acetal) precursor under basic conditions. However, the synthesis was lengthy with low-yielding steps, which led to it being abandoned. The second route involved generation of 1,2-bis(5-isobenzofuranyl)ethene from a bis(oxabicyclic) precursor with 3,6-di(2'-pyridyl)-s-tetrazine. Napththo[1,2-c:5,6-c] difuran and 1,2-bis(5isobenzofuranyl)ethene were used to construct novel cyclophanes by double Diels-Alder reactions with bis(maleimide)s. NMR, AM1 modeling, and X-ray studies of the cyclophanes are discused. Attempts to prepare phenanthro[2,3-c:6,7-c] difuran and its cyclophanes are discussed. None was successful, and investigations were hampered by the inability to obtain sufficient quantities of starting materials. Finally, several suggestions are given for improving the syntheses of 1,2-bis(5-
isobenzofuranyl)ethene, phenanthro[2,3-c:6,7-c]difuran, and their cyclophanes. Future directions, such as the functionalization of the double bond of 1,2-bis(5-isobenzofuranyl)ethene, aromatization of the oxabicyclic rings of the cyclophanes, and further X-ray studies are discussed. / x, 122 leaves : ill. ; 28 cm.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:ALU.w.uleth.ca/dspace#10133/239
Date January 2003
CreatorsThibault, Michelle Elizabeth, University of Lethbridge. Faculty of Arts and Science
ContributorsDibble, Peter
PublisherLethbridge, Alta. : University of Lethbridge, Faculty of Arts and Science, 2003, Arts and Science, Department of Chemistry and Biochemistry
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
Languageen_US
Detected LanguageEnglish
TypeThesis
RelationThesis (University of Lethbridge. Faculty of Arts and Science)

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