|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