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

Fingerprint

Silicon
Carbon
Benzene
analogs
carbon
benzene
silicon
synthesis
Strain energy
trienes
rings
Bond length
Names
isolation
Atoms
energy
atoms

Keywords

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

ASJC Scopus subject areas

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

Cite this

Tajima, T., Hatano, K., Sasaki, T., Sasamori, T., Takeda, N., Tokitoh, 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

Syntheses and structures of silicon analogues of cyclopropabenzenes. / Tajima, Tomoyuki; Hatano, Ken; Sasaki, Takayo; Sasamori, Takahiro; Takeda, Nobuhiro; Tokitoh, Norihiro; Takagi, Nozomi; Nagase, Shigeru.

In: Journal of Organometallic Chemistry, Vol. 686, No. 1-2, 01.12.2003, p. 118-126.

Research output: Contribution to journalArticle

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, vol. 686, no. 1-2, pp. 118-126. https://doi.org/10.1016/S0022-328X(03)00446-7
Tajima, Tomoyuki ; Hatano, Ken ; Sasaki, Takayo ; Sasamori, Takahiro ; Takeda, Nobuhiro ; Tokitoh, Norihiro ; Takagi, Nozomi ; Nagase, Shigeru. / Syntheses and structures of silicon analogues of cyclopropabenzenes. In: Journal of Organometallic Chemistry. 2003 ; Vol. 686, No. 1-2. pp. 118-126.
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