Effects of Substituents on the Formation of Acetals of 4-Substituted 1,3-Indandiones
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概要
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Treatment of 4-nitrol,3-indandione (<B>1</B>) with an equivalent of ethylene glycol in benzene in the presence of <I>p</I>-toluenesulfonic acid afforded 4-nitro-1,3-indandione-1-ethylene acetal (<B>2</B>), 3-ethylene acetal (<B>3</B>) and 1,3-bisethylene acetal (<B>4</B>). Kinetic studies revealed that <B>2</B> is a kinetically preferred product and <B>3</B> is a thermodynamically preferred product. However, the reaction of 4-acetamido-1,3-indandione (<B>5</B>) with ethylene glycol under similar conditions gave 4-acetamido-1,3-indandione-1-ethylene acetal (<B>6</B>) as a product both kinetically and thermodynamically controlled. Thioacetalization of <B>1</B> with an equivalent of 1,2-ethanedithiol afforded selectively 4-nitro-1,3-indandione-1-ethylene thioacetal (<B>9</B>).
- 公益社団法人 日本化学会の論文
著者
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Otsuji Yoshio
Department Of Applied Chemistry College Of Engineering University Of Osaka Prefecture
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Imoto Eiji
Department of Applied Chemistry College of Engineering The University of Osaka Prefecture
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Sakane Kazuo
Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture
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