Synthesis of 4,6-dimethyl-tetrahydro- and hexahydro-dibenzothiophene |
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Authors: | Yinyong Sun |
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Affiliation: | Institute of Chemical and Bioengineering, ETH Zurich, 8093 Zurich, Switzerland |
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Abstract: | 2-Bromo-3-methylcyclohexanone was synthesized by conjugate addition of trimethylaluminium to 2-bromo-2-cyclohexen-1-one with copper bromide as catalyst, coupled with 2-methylthiophenol and annulated with the aid of polyphosphoric acid to 4,6-dimethyl-1,2,3,4-tetrahydrodibenzothiophene. The latter was hydrogenated to 4,6-dimethyl-1,2,3,4,4a,9b-hexahydrodibenzothiophene, another intermediate in the hydrodesulfurization of 4,6-dimethyldibenzothiophene, by zinc and trifluoroacetic acid, and dehydrogenated to 4,6-dimethyldibenzothiophene. |
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Keywords: | Conjugate addition 2-Bromo-3-methylcyclohexanone Tilak annulation 4,6-Dimethyldibenzothiophene |
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