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Stannabenzene : ウィキペディア英語版
Stannabenzene

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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, 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()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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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 () 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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