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<p>The reaction of dicyclopropylacetylene with excess diazomethane in the presence of copper compounds leads successively first to dicyclopropylcyclopropene resulting from multiple bond cyclopropanation and then to 1,3-dicyclopropylbicyclo[1.1.0]butane. The latter under the reaction conditions partially isomerizes to 2,3-dicyclopropylbuta-1,3-diene, which, in turn, undergoes further cyclopropanation. As a result, when an 8–10-fold excess of diazomethane is used, a hydrocarbon of the 1,1-oligocyclopropane series, 1,1′-dicyclopropylbicyclopropane (ivyane[4]), is formed. Monocyclopropanation of dicyclopropylbutadiene readily proceeds in the presence of Pd(acac)<sub>2</sub>, whereas cyclopropanation of the second double bond occurs only with a large excess of diazomethane.</p>

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Catalytic reaction of dicyclopropylacetylene with diazomethane: synthesis of ivyane[4]

  • 期刊论文

  • 发表日期：

    2025年3月1日

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  • E. V. Shulishov,
  • O. A. Pantyukh,
  • E. D. Streltsova,
  • L. G. Menchikov,
  • Yu. V. Tomilov

摘要

The reaction of dicyclopropylacetylene with excess diazomethane in the presence of copper compounds leads successively first to dicyclopropylcyclopropene resulting from multiple bond cyclopropanation and then to 1,3-dicyclopropylbicyclo[1.1.0]butane. The latter under the reaction conditions partially isomerizes to 2,3-dicyclopropylbuta-1,3-diene, which, in turn, undergoes further cyclopropanation. As a result, when an 8–10-fold excess of diazomethane is used, a hydrocarbon of the 1,1-oligocyclopropane series, 1,1′-dicyclopropylbicyclopropane (ivyane[4]), is formed. Monocyclopropanation of dicyclopropylbutadiene readily proceeds in the presence of Pd(acac)2, whereas cyclopropanation of the second double bond occurs only with a large excess of diazomethane.