In recent years, however, a kinetically stabilized silabenzene and other heavy aromatic compounds with silicon or germanium atoms have been reported.
In 1978 Barton and Burns reported that flow pyrolysis of 1‑methyl-1‑allyl-1‑silacyclohexa-2,4‑diene through a quartz tube heated to 428 °C using either ethyne or perfluoro-2-butyne as both a reactant and a carrier gas afforded the methyl-1‑silylbenzene Diel-Alder adducts, 1‑methyl-1‑silabicyclo[2.2.2]octatriene or 1‑methyl-2,3‑bis(trifluoromethyl)-1‑silabicyclo[2.2.2]octatriene, respectively, by way of a retro-ene reaction.
[3] The [1,3]-Si → O shift of TMS or triisopropylsilyl (TIPS) substituted precursors with tetrahedral silicon atoms to an adjacent carbonyl oxygen lead to aromatic Brook-type silabenzenes.
Silicon is a semi-metal element, so the Si-C π bond in the silabenzene is highly polarized and easily broken.
The searching of a planar Si6 analogue to benzene has been extended to anionic cycles and structures bearing lithium atoms replacing hydrogens.
[21] The nucleus-independent chemical shifts (NICS)[22] was selected as the quantitative criterion to evaluate the aromatic character of the structures under study.