The reaction of cyclic 1,3-diketones with alkylthiocyclopropenium ions to yield 2-alkylthio-substituted 2H-pyrans.
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概要
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This study treats the reactions of methylthio-, ethylthio-, or benzylthiodiphenylcyclopropenium ion (<B>1</B>) with 5-, 6-, and 7-membered cyclic 1,3-diketones, giving either 2-alkylthio-2<I>H</I>-pyrans or dienone derivarives. Treatment of <B>1</B> with 1,3-cyclopentanedione, 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, 4-hydroxy-6-methyl-2-pyrone, 4-hydroxycoumarin, and 1,3-cycloheptanedione in the presence of triethylamine afforded 2-alkylthio-2<I>H</I>-pyrans. The structure of the products was elucidated on the basis of their elemental analyses, IR, <SUP>1</SUP>H-NMR, <SUP>13</SUP>C-NMR, and mass spectroscopic data, as well as chemical transformations. 2-Alkylthio-2<I>H</I>-pyrans with mercury(II) chloride in an alcohol underwent conversion to the corresponding 2-alkoxy-2<I>H</I>-pyrans. The <SUP>1</SUP>H- and <SUP>13</SUP>C-NMR data of these compounds clearly show that the equilibrium lies completely on the side of the 2<I>H</I>-pyran. In contrast, the reaction of <B>1</B> with 1,3-indandione yielded the ring-opened dienone derivative as a mixture of <I>E</I> and <I>Z</I> isomers.
- 公益社団法人 日本化学会の論文
著者
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Yoshida Hiroshi
Departmen Of Radiology School Of Medicine Asahikawa Medical University
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Matsumoto Kiyoshi
College of Liberal Arts and Sciences, Kyoto University
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Ogata Tsuyoshi
Department of Applied Chemistry, Faculty of Engineering, Shizuoka University
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Nakajima Mikito
Department of Applied Chemistry, Faculty of Engineering, Shizuoka University
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