Syntheses and structures of silicon analogues of cyclopropabenzenes

Tomoyuki Tajima, Ken Hatano, Takayo Sasaki, Takahiro Sasamori, Nobuhiro Takeda, Norihiro Tokitoh, Nozomi Takagi, Shigeru Nagase

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The reactions of an overcrowded diaryldilithiosilane, Tbt(Dip)SiLi 2 (Tbt=2,4,6-tris[bis(trimethylsilyl)methyl]phenyl; Dip=2,6-diisopropylphenyl), with o-dibromobenzene and 1,2,4, 5-tetrabromobenzene resulted in the synthesis and isolation of the first stable silacyclopropabenzene and bis(silacyclopropa)benzenes (IUPAC name is 4,8-disilatricyclo[5.1.0.03,5]octa-1,3(5), 6-triene), respectively. The crystallographic analyses and theoretical calculations revealed that the lengths of the juncture carbon-carbon bonds of the mono- and bis(silacyclopropa)benzenes were marginally in the range of carbon-carbon bond lengths of usual benzene rings. It is shown that this structural feature is attributable to a decrease in the strain energy of silacyclopropabenzenes relative to the corresponding cyclopropabenzenes, and the strain energy is a simple additive function of the number of the fused three-membered rings involving Si atom.

Original languageEnglish
Pages (from-to)118-126
Number of pages9
JournalJournal of Organometallic Chemistry
Volume686
Issue number1-2
DOIs
Publication statusPublished - Dec 1 2003
Externally publishedYes

Keywords

  • Bis(silacyclopropa)benzenes
  • Crystallographic structural analysis
  • Diaryldilithiosilane
  • Silacyclopropabenzene
  • Three-membered ring

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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  • Cite this

    Tajima, T., Hatano, K., Sasaki, T., Sasamori, T., Takeda, N., Tokitoh, N., Takagi, N., & Nagase, S. (2003). Syntheses and structures of silicon analogues of cyclopropabenzenes. Journal of Organometallic Chemistry, 686(1-2), 118-126. https://doi.org/10.1016/S0022-328X(03)00446-7