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 language | English |
|---|---|
| Pages (from-to) | 118-126 |
| Number of pages | 9 |
| Journal | Journal of Organometallic Chemistry |
| Volume | 686 |
| Issue number | 1-2 |
| DOIs | |
| Publication status | Published - Dec 1 2003 |
| Externally published | Yes |
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