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<p>Reaction of readily available 1-aryl-1-chlorocyclopropanes with alcohols in the KOH—DMSO system at 80–100 °C affords corresponding 1-alkoxy-2-arylcyclopropanes in up to 92% yield. The procedure is simple to implement, provides high stereoselectivity, and in most cases allows one to obtain products with <i>trans</i>-arrangement of the alkoxy group and aryl fragment. The results obtained suggest that isomerization of 1-alkoxy-2-arylcyclopropanes can occur under the strongly basic conditions used due to inversion of the configuration of the cyclopropane carbon atom located at the aromatic substituent.</p>

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Reaction of 1-aryl-1-chlorocyclopropanes with alcohols in KOH—DMSO system as a stereoselective method for the synthesis of 1-alkoxy-2-arylcyclopropanes

  • 期刊论文

  • 发表日期：

    2025年10月1日

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  • V. D. Gvozdev,
  • K. N. Shavrin,
  • M. P. Egorov

摘要

Reaction of readily available 1-aryl-1-chlorocyclopropanes with alcohols in the KOH—DMSO system at 80–100 °C affords corresponding 1-alkoxy-2-arylcyclopropanes in up to 92% yield. The procedure is simple to implement, provides high stereoselectivity, and in most cases allows one to obtain products with trans-arrangement of the alkoxy group and aryl fragment. The results obtained suggest that isomerization of 1-alkoxy-2-arylcyclopropanes can occur under the strongly basic conditions used due to inversion of the configuration of the cyclopropane carbon atom located at the aromatic substituent.