Stannabenzene Explained

Stannabenzene (C₅H₆Sn) 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,^[1] but has not been isolated.

Stable derivatives of stannabenzene

Stable derivatives of stannabenzene have been isolated. The 2-stannanaphthalene depicted below is stable in an inert atmosphere at temperatures below 140 °C.^[2] 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.^[3] At room temperature it forms the [4+2] cycloadduct.

Tbt-substituted stannabenzene was reported in 2010.^[4] At room-temperature it quantitatively forms the DA dimer.

See also

• 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, bismabenzene, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium

Notes and References

1. 10.1016/j.theochem.2009.10.038 . Ebrahimi, Arash Afshar . Ghiasi, Reza . Foroutan-Nejad, Cina . Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes . Journal of Molecular Structure: THEOCHEM . 2010 . 941 . 1–3 . 47–52.
2. Mizuhata . Yoshiyuki . Sasamori . Takahiro . Takeda . Nobuhiro . Tokitoh . Norihiro . A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene . Journal of the American Chemical Society . 128 . 1050–1 . 2006 . 10.1021/ja057531d . 4 . 16433501.
3. Generation of 9-Stannaphenanthrene and Its Reactivities Yoshiyuki Mizuhata, Nobuhiro Takeda, Takahiro Sasamori and Norihiro Tokitoh Chemistry Letters Volume 34 Number 8 Year 2005 Page 1088
4. Generation of Stannabenzenes and Their Properties Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784