THE [4 + 2]CYCLOADDITION REACTIONS OF AROMATIC THIONES WITH MALEIC ANHYDRIDE,NORBORNENE, AND NORBORNADIENE |
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| Authors: | Haruo Ohmura Shinichi Motoki |
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| Institution: | Department of Chemistry, Faculty of Science , Science University of Tokyo , Kagurazaka, Shinjuku-ku, Tokyo, 162, Japan |
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| Abstract: | Abstract The reactions of aryl 1-naphthyl thiones and aryl 2-naphthyl thiones with maleic anhydride, norbornene, and norbornadiene gave the 1,4-cycloadducts containing 3,4-dihydro-2 H-thiopyran rings. 7H-Benzde]anthracene-7-thione also reacted with norbornene and norbornadiene to give similar 1,4-cycloadducts. In the reaction of aryl phenyl thiones with norbornene, initially formed cycloadducts rearranged to aromatized compounds. In these reactions, the aromatic thiones reacted with the olefins as a heterodiene system. |
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| Keywords: | Quinones Phosphorus pentachloride Mechanism Infrared Dimethylaniline Mass spectra |
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