Stannabenzene

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.

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.

[4] At room-temperature it quantitatively forms the DA dimer.

A stable 2-stannanaphthalene derivative
Tbt-substituted stannabenzene synthesis. Reagents lithium aluminium hydride (step 2), NBS (step 3), LDA (step 4)