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Synthesis and spectral studies of methyl heterocylic systems

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dc.contributor.author Doyle, Paul P. en_US
dc.date.accessioned 2009-07-09T18:43:11Z
dc.date.available 2009-07-09T18:43:11Z
dc.date.issued 1979-07-09T18:43:11Z
dc.identifier.uri http://hdl.handle.net/10464/2085
dc.description.abstract 2-Carboxy-2?-methyldiphenyl sulfide was prepared by the Ullmann reaction and cyclodehydrated by sulfuric acid to afford 4-methylthioxanthone. 1-Methylthioxanthone was separated from the reaction mixture obtained upon cyclodehydration of 2-carboxy-3f-methyldiphenyl sulfide. In addition, 1-, 2-, 3- and 4-methylthioxanthone 10,10-dioxides were synthesized by oxidation of the corresponding thioxanthones. o-, m- and p-N-Tolylanthranilic acids were prepared by the Ullmann reaction and used as precursors for the preparation of 1-, 2- and 4- methyl-9-chloroacridine and finally 1-, 2-, 3- and 4-methylacridone. High resolution, 60 MHz PMR spectra were obtained on the four monomethyl isomers of xanthone, thioxanthone, thioxanthone 10,10-dioxide and acridone, and on 1-, 2- and 4-methyl-9-chloroacridine. For some compounds, coupling of all three different aromatic protons to the methyl was observed, two of the couplings typically being smaller than the third. With the large (ortho) coupling being on the order of 0.5 to 1.0 Hz, it was necessary to decouple the aromatic part of the spectrum. The magnitude of the ortho benzylic constant may be related to an incomplete Tr-bond delocalization in the molecules. en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Heterocyclic compounds--Spectra. en_US
dc.subject Methyl groups--Spectra. en_US
dc.subject Spectrum analysis. en_US
dc.subject Organic compounds--Synthesis. en_US
dc.title Synthesis and spectral studies of methyl heterocylic systems en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name M.Sc. Chemistry en_US
dc.degree.level Masters en_US
dc.contributor.department Department of Chemistry en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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