Stannabenzene (C5H6Sn) is the parent representative of a group oforganotin compounds that are related tobenzene with acarbon atom replaced by atin atom. Stannabenzene itself has been studied bycomputational chemistry,[1] 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 °C.[2] The tin to carbon bond in this compound is shielded from potential reactants by two very bulky groups, onetert-butyl group and the even larger 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl or Tbt group. The two Sn-C bonds havebond lengths of 202.9 and 208.1pm which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=Cdouble 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 isaromatic.
A stable 2-stannanaphthalene derivative
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 theDA dimer.
^Ebrahimi, Arash Afshar; Ghiasi, Reza; Foroutan-Nejad, Cina (2010). "Topological characteristics of the ring critical points and the aromaticity of groups IIIA to VIA hetero-benzenes".Journal of Molecular Structure: THEOCHEM.941 (1–3):47–52.doi:10.1016/j.theochem.2009.10.038.
^Mizuhata, Yoshiyuki; Sasamori, Takahiro; Takeda, Nobuhiro; Tokitoh, Norihiro (2006). "A Stable Neutral Stannaaromatic Compound: Synthesis, Structure and Complexation of a Kinetically Stabilized 2-Stannanaphthalene".Journal of the American Chemical Society.128 (4):1050–1.doi:10.1021/ja057531d.PMID16433501.
^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 1088doi:10.1246/cl.2005.1088
^Generation of Stannabenzenes and Their Properties Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784doi:10.1021/om100382n
