Stannabenzene (C5H6Sn) is the parent representative of a group of chemical compounds containing in their molecular structure a benzene ring with a carbon atom replaced by a tin atom. Stannabenzene (1) itself is still elusive but stable naphthalene derivatives do exist in the laboratory. The 2-Stannanaphthalene 2 is stable in an inert atmosphere at temperatures below 140 °C. The tin to carbon bond in this compound is shielded from potential reactants by 2 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 p.m.) and comparable to that of known Sn=C double bonds (201.6 p.m.). The C-C bonds show little variation with bond lengths between 135.6 and 144.3 p.m. signaling that this compound is aromatic.
- 6-membered aromatic rings with one carbon replaced by another group: borabenzene, benzene, silabenzene, germanabenzene, stannabenzene, pyridine, phosphorine, pyrylium salt
- ^ . A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene Yoshiyuki Mizuhata, Takahiro Sasamori, Nobuhiro Takeda, and Norihiro Tokitoh J. Am. Chem. Soc.; 2006; 128(4) pp 1050 - 1051; Article