Stannabenzene Mizuhata 2010 on:
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Stannabenzene (C5H6Sn) is the parent representative of a group of
Tbt-substituted 9-stannaphenanthrene was reported in 2005. At room temperature it forms the +2 cycloadduct.
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.
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organotin compound
Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide (), discovered by ...
s that are related to benzene with a carbon atom replaced by a tin atom. Stannabenzene itself has been studied by computational chemistry
Computational chemistry is a branch of chemistry that uses computer simulation to assist in solving chemical problems. It uses methods of theoretical chemistry, incorporated into computer programs, to calculate the structures and properties of m ...
, 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. 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 is(trimethylsilyl)methylhenyl 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 +2 cycloadduct.
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.
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See also
* 6-membered aromatic rings with one carbon replaced by another group: borabenzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene,bismabenzene
Bismabenzene () is the parent representative of a group of organobismuth compounds that are related to benzene with a carbon atom replaced by a bismuth atom. Bismabenzene itself has been synthesised but not isolated because it is too reactive, te ...
, pyrylium, thiopyrylium, selenopyrylium, telluropyrylium
References
{{reflist Tin heterocycles Six-membered rings Hypothetical chemical compounds Tin(IV) compounds