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

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

Creators Kajigaeshi Shoji

Creators Matsumoto Goro

Creators Nishida Akiko

Creators Fujisaki Shizuo

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.

[ISSN]0372-7661

[NCID]AN00244228