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Abstract <p>The reaction of 1-phenyl-1,2-dicarba-<i>closo</i>-dodecaborane with <i>n</i>-butyllithium at –75°C in tetrahydrofuran followed by addition of acetyl chloride leads to 1-(2′-phenyl-1′,2′-dicarba-<i>closo</i>-dodecaboran-1′-yl)-vinyl acetate instead of the expected (2-phenyl-1,2-dicarba-<i>closo</i>-dodecaboran-1-yl)methyl ketone. The product structure was characterized by NMR spectroscopy, IR spectroscopy, and single crystal X-ray diffraction analysis. A mechanism for this transformation was proposed and confirmed by quantum chemical calculations.</p>

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Synthesis and Crystal Structure of 1-(2′-Phenyl-1′,2′-dicarba-closo-dodecaboran-1′-yl)-vinyl Acetate

  • 期刊论文

  • 发表日期：

    2026年3月19日

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  • Anna A. Druzina,
  • Olga B. Zhidkova,
  • Sergey A. Anufriev,
  • Aleksey S. Romanenko,
  • Ivan V. Ananyev,
  • Igor B. Sivaev,
  • Vladimir I. Bregadze

摘要

Abstract

The reaction of 1-phenyl-1,2-dicarba-closo-dodecaborane with n-butyllithium at –75°C in tetrahydrofuran followed by addition of acetyl chloride leads to 1-(2′-phenyl-1′,2′-dicarba-closo-dodecaboran-1′-yl)-vinyl acetate instead of the expected (2-phenyl-1,2-dicarba-closo-dodecaboran-1-yl)methyl ketone. The product structure was characterized by NMR spectroscopy, IR spectroscopy, and single crystal X-ray diffraction analysis. A mechanism for this transformation was proposed and confirmed by quantum chemical calculations.