Stannabenzene (C<sub>5</sub>H<sub>6</sub>Sn) is the parent representative of a group of organotin compounds that are related to benzene with a carbon atom replaced by a tin atom. Stannabenzene itself has been studied by computational chemistry, but has not been isolated.
Stable derivatives of stannabenzene have been isolated. The 2-stannanaphthalene depicted below is stable in an inert atmosphere at temperatures below 140 ðC. The tin to carbon bond in this compound is shielded from potential reactants by two very bulky groups, one tert-butyl group and the even larger 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl or Tbt group. The two Sn-C bonds have bond lengths of 202.9 and 208.1 pm which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=C double bonds (201.6 pm). The C-C bonds show little variation with bond lengths between 135.6 and 144.3 pm signaling that this compound is aromatic.
Tbt-substituted 9-stannaphenanthrene was reported in 2005. At room temperature it forms the [4+2] cycloadduct.
Tbt-substituted stannabenzene was reported in 2010. At room-temperature it quantitatively forms the DA dimer.