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Abstract <p>A previously unknown family of 9-selenabicyclo[4.2.1]nonane derivatives was obtained in up to 98% yields by the transannular addition reaction of selenium dihalides with 1,3-cyclooctadiene. Conditions for selective <i>anti,anti</i> and <i>syn,anti</i> (<i>endo–exo</i> diastereomer) additions to obtain the <i>endo–endo</i> or <i>endo–exo</i> diastereomers, respectively, were found. An approach to selectively introducing two target substituents into selenabicyclo[4.2.1]nonane, including isomerization of the <i>endo–exo</i> diastereomer into the <i>endo–endo</i> derivative, was developed.</p>

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Synthesis of New Derivatives of 9-Selenabicyclo[4.2.1]nonane by the Transannular Addition of Selenium Dihalides to 1,3-Cyclooctadiene

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  • 发表日期：

    2025年11月1日

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  • M. V. Musalov,
  • A. A. Pakeeva,
  • V. A. Potapov

摘要

Abstract

A previously unknown family of 9-selenabicyclo[4.2.1]nonane derivatives was obtained in up to 98% yields by the transannular addition reaction of selenium dihalides with 1,3-cyclooctadiene. Conditions for selective anti,anti and syn,anti (endo–exo diastereomer) additions to obtain the endo–endo or endo–exo diastereomers, respectively, were found. An approach to selectively introducing two target substituents into selenabicyclo[4.2.1]nonane, including isomerization of the endo–exo diastereomer into the endo–endo derivative, was developed.