2026-09-20T18:52:18.580361300Zhttps://opus.uleth.ca/server/oai/requestoai:opus.uleth.ca:10133/7812019-06-12T17:31:40Zcom_10133_3346com_10133_1com_10133_296col_10133_3347col_10133_298
ULethbridge OPUS Repository
supervisor
Dibble, Peter W.
supervisor
Boeré, René T.
author
Robbins, Steven J.
author
University of Lethbridge. Faculty of Arts and Science
2009-10-13T15:45:49Z
2009-10-13T15:45:49Z
2009
https://hdl.handle.net/10133/781
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_US
Cyclophanes -- Synthesis
Dissertations, Academic
Cyclophanes from kinetically stabilized bis(isobenzofuran)s
Thesis
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URL
http://localhost:4000/bitstreams/5aa32d0f-3bd5-4a07-af22-90905e338ee5/download
File
MD5
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application/pdf
ROBBINS_STEVEN_MSC_2009.pdf
URL
http://localhost:4000/bitstreams/884d44d2-c081-4732-9ceb-3a2e0fb2f239/download
File
MD5
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ROBBINS_STEVEN_MSC_2009.pdf.txt