Experimental evidence and bond characterization of a cyclopropenylgermylene

Shinobu Tsutsui, Hiromasa Tanaka, Eunsang Kwon, Shigeki Matsumoto, Kenkichi Sakamoto

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6 Citations (Scopus)


The reduction of p-anisyl(1,2,3-tri-tert-butylcycloprop-2-en-1-yl)dichlorogermane (1) with potassium in the presence of an excess of tert-butyldimethylsilane in benzene under reflux gave p-anisyl(tert-butyldimethylsilyl)(1,2,3-tri-tert-butylcycloprop-2-en-1-yl) germane (4) in 15% yield. The formation of 4 indicates that p-anisyl(1,2,3-tri-tert-butylcycloprop-2-en-1-yl)germylene (2), which is the first example of a (cycloprop-2-en-1-yl)germylene derivative, was generated and trapped by the hydrosilane. The DFT calculations revealed that the cis-2-p-anisyl-1,3,4-tri-tert-butyl-2-germabicyclo[1.1.0]butane-2,4-diyl structure cis-5 is 8.0 kJ/mol more stable than cis-2. The NBO analysis revealed that cis-5 has a 2-germabicyclo[1.1.0]butane diradical character.

Original languageEnglish
Pages (from-to)595-603
Number of pages9
JournalJournal of Organometallic Chemistry
Issue number4
Publication statusPublished - 2006 Feb 1


  • Cyclopropene
  • Density functional theory
  • Germylene
  • Natural bond orbital analysis
  • Organogermanium compound


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