Cyclophanes from kinetically stabilized bis(isobenzofuran)s
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Date
2009
Authors
Robbins, Steven J.
University of Lethbridge. Faculty of Arts and Science
Journal Title
Journal ISSN
Volume Title
Publisher
Lethbridge, Alta. : University of Lethbridge, Deptartment of Chemistry and Biochemistry, 2009
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.
Description
xxii, 122 leaves : ill. ; 29 cm.
Keywords
Cyclophanes -- Synthesis , Dissertations, Academic