Stannabenzene
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| Names | |||
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| IUPAC name
Stannine
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| Other names
Stannin
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| Identifiers | |||
289-78-1  |
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| ChemSpider | 20137777  |
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| Properties | |||
| C5H6Sn | |||
| Molar mass | 184.81 g·mol−1 | ||
| Vapor pressure | {{{value}}} | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
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File:Stannabenzene derivative.svgA 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 the DA dimer.
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File:Stannabenzene Mizuhata 2010.svgTbt-substituted stannabenzene synthesis. Reagents lithium aluminum hydride (step 2), NBS (step 3), LDA (step 4)
See also
- 6-membered aromatic rings with one carbon replaced by another group: borabenzene, benzene, silabenzene, germabenzene, stannabenzene, pyridine, phosphorine, arsabenzene, pyrylium salt
References
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- ↑ 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 doi:10.1246/cl.2005.1088
- ↑ Generation of Stannabenzenes and Their Properties Yoshiyuki Mizuhata, Naoya Noda, and Norihiro Tokitoh Organometallics, 2010, 29 (21), pp 4781–4784 doi: 10.1021/om100382n
