Memoirs of the Faculty of Engineering, Yamaguchi University

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Memoirs of the Faculty of Engineering, Yamaguchi University Volume 40 Issue 1
published_at 1989-10

Ring Opening of 1,1-Dichloro-2-methyl-2-phenylsulfonylcyclopropane Derivatives with Sodium Alkoxide

1,1-ジクロロ-2-メチル-2-フェニルスルホニルシクロプロパン誘導体のナトリウムアルコキシドによる開環
Kajigaeshi Shoji
Matsumoto Goro
Nishida Akiko
Fujisaki Shizuo
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About This Article
Descriptions
Oxidations of 1,1-dichloro-2-methyl-2-phenylmercaptocyclopropane derivatives [15]-[20] with hydrogen peroxide in acetic acid gave the corresponding 1,1-dichloro-2-methyl-2-phenylsulfonylcyclopropane derivatives [1]-[6]. Reactions of [1]-[6] with sodium methoxide in methanol or sodium ethoxide in ethanol under reflux gave a mixture of phenylsulfinic acid and unstable compounds such acetyleneketals and ketoacetylenes as ring opening products. Reactions of both trans-and cis-1,1-dichloro-3-phenyl-2-phenylsulfonylcyclopropane with sodium methoxide in methanol gave same cis-1,1-dimethoxy-3-phenyl-2-phenylsulfonylcyclopropane [30], respectively, The above reaction mechanism was also discussed.
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