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Experimental evidence and bond characterization of a cyclopropenylgermylene

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
691
Issue
4
Identifiers
DOI: 10.1016/j.jorganchem.2005.09.041
Keywords
  • Organogermanium Compound
  • Germylene
  • Cyclopropene
  • Density Functional Theory
  • Natural Bond Orbital Analysis

Abstract

Abstract 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.

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