The Rearrangement of 10-Bromo-10,11-dihydrodibenzo[<I>b</I>,<I>f</I>]thiepin-11-one and Related Compounds in an Alkaline Solution
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概要
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The reaction of 10-bromo-10,11-dihydrodibenzo[<I>b</I>,<I>f</I>]thiepin-11-one (<B>1</B>) with sodium methoxide in methanol has been shown to lead to thioxanthone (<B>4</B>) and 10-hydroxy-10,11-dihydrodibenzo[<I>b</I>,<I>f</I>]thiepin-11-one (<B>5</B>). If the reaction of <B>1</B> in an aqueous sodium hydroxide solution is carried out, six products, <B>4</B>, <B>5</B>, 9-hydroxy-thioxanthene-9-carboxylic acid (<B>6</B>), thioxanthene-9-carboxylic acid (<B>7</B>), thioxanthene (<B>8</B>), and 10,11-dihydrodibenzo [<I>b</I>,<I>f</I>]thiepin-10-one (<B>9</B>), are formed. The structures of the products were established by elementary analysis, by an examination of the spectral data, by gas chromatography, and by an independent synthesis. The results were discussed in terms of the mechanism proposed.
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