Silabenzene

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.

Structural formula of silabenzene
Ball-and-stick model of the Silabenzene molecule
Structures of some unstable silabenzenes
Stable 2-silanaphthalene and silabenzene