Synthesis and investigation of biphenylene planarized aromatic and anti-aromatic systems
Item
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Title
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Synthesis and investigation of biphenylene planarized aromatic and anti-aromatic systems
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Identifier
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d_2009_2013:09998e9b53e5:11458
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identifier
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11904
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Creator
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Wu, Youchun,
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Contributor
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Klaus Grohmann
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Date
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2012
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Language
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English
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Publisher
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City University of New York.
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Subject
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Organic chemistry
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Abstract
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The aim of the dissertation was to develop synthetic routes to biphenylene planarized aromatic and anti-aromatic systems such as bis(diacetylene)biphenylene 109, and 4,5,6,7-dibenzocyclobutathionin(biphenylenothionin) 110. Bis(diacetylene)anthracene 209 was prepared by Nakagawa by dimerization of 1,8-diethynylanthracene 208..;In the first part of this dissertation, biphenylene systems were synthesized by different methods: by aryne generation, coupling a biphenyl and by extrusion of gas. Key intermediate 1, 8-diacetylene biphenylene 114 was synthesized successfully by coupling dihalo substituted biphenylene and alkyne.;Nucleophilic addition of sulfide ion to 1, 8-diacetylene biphenylene 114, instead of an expected nine-membered ring compound 4,5,6,7-dibenzocyclobutathionin 110, gave an unexpected eight-membered ring compound (Z)-1-methylene-1 H-biphenyleno[1,8-cde]thiocine 189, with structure confirmed by DEPT 13C NMR, IR , X-ray and GC-MS.;Two comparisons of 4,5,6,7-dibenzocyclobutathionin 110, (Z)-5, 6-dihydrodibenzo[d,f]thionine 111 and dibenzo[ d,f]thionine 112, were synthesized and NMR data were analyzed and compared.
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Type
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dissertation
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Source
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2009_2013.csv
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degree
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Ph.D.
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Program
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Chemistry
