Organotin Compounds

"Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry.^[1] The first organotin compound was diethyltin diiodide, discovered by Edward Frankland in 1849. An organotin compound is commercially applied as a hydrochloric acid scavenger (or heat stabilizer) in polyvinyl chloride and as a biocide. Tributyltin oxide has been extensively used as a wood preservative. Tributyltin compounds are used as marine anti-biofouling agents. Concerns over toxicity^[2] of these compounds (some reports describe biological effects to marine life at a concentration of 1 nanogram per liter) have led to a worldwide ban by the International Maritime Organization. n-Butyltin trichloride is used in the production of tin dioxide layers on glass bottles by chemical vapor deposition."

"Organotin compounds are generally classified according to their oxidation states. Tin(IV) compounds are much more common and more useful."

"Compounds of Sn(I) are rare and only observed with very bulky ligands. One prominent family of cages is accessed by pyrolysis of the 2,6-diethylphenyl-substituted tristannylene [Sn(C₆H₃-2,6-Et₂)₂]₃, which affords the cubane and a prismane. These cages contain Sn(I) and have the formula [Sn(C₆H₃-2,6-Et₂)]_n where n = 8, 10.^[9] A stannyne contains a carbon to tin triple bond and a distannyne a triple bond between two tin atoms (RSnSnR). Distannynes only exist for extremely bulky substituents. Unlike alkynes, the C-Sn-Sn-C core of these distannynes are nonlinear, although they are planar. The Sn-Sn distance is 3.066(1) Å, and the Sn-Sn-C angles are 99.25(14)°. Such compounds are prepared by reduction of bulky aryltin(II) halides."