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,
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.
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-trisbis(trimethylsilyl)methylphenyl or Tbt group. The two Sn-C bonds have
of 202.9 and 208.1
picometer which are shorter than those for Sn-C single bonds (214 pm) and comparable to that of known Sn=C
(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.[ 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 ] At room temperature it forms the 4+2 cycloaddition.
Tbt-substituted stannabenzene was reported in 2010.[ Generation of Stannabenzenes and Their Properties Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784 ] At room-temperature it quantitatively forms the DA dimer.
- (step 2), NBS (step 3), LDA (step 4) ]]
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
