A facile ring enlargement reaction via .BETA.-oxido carbenoid.

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概要

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• A general method of transforming a cyclic ketone to the next higher ring homolog chlorinated at the α-carbon or alternatively to its parent ketone is described. Treatment of a dichloromethyllithium-carbonyl adduct <B>2</B> with butyllithium affords a β-oxido carbenoid <B>3</B> at low temperature. Upon warming, <B>3</B> decomposes to a lithium enolate <B>4</B>, which is quenched with diluted hydrochloric acid to give the α-chloro ketone <B>5</B>. Cycloalkanone is converted to a one-carbon ring enlarged halogenated ketone. Meanwhile, dibromomethylcarbinol <B>7</B> is transformed to the halogen-free ketone <B>8</B> <I>via</I> monobromo β-oxido carbenoid upon treatment with butyllithium. α-Methyl substituted ketone is exclusively converted to the β-methyl substituted homolog and therefore <I>dl</I>-muscone is synthesized from cyclotetradecanone according to this new method.

• 公益社団法人 日本化学会の論文

著者

• Yamamoto Hisashi

  Department Applied Chemistry Nagoya University

• Nozaki Hitosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

• Taguchi Hiroaki

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

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