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 ((C2H5)2SnI2), discovered by Edward Frankland in 1849. The area grew rapidly in the 1900s, especially after the discovery of the Grignard reagents, which are useful for producing Sn-C bonds. The area remains rich with many applications in industry and continuing activity in the research laboratory.
Organotin compounds are generally classified according to their oxidation states. Tin(IV) compounds are much more common and more useful.
The entire series R4−nSnCln are known for many R groups and values of n up to 4. The tetraorgano derivatives are invariably tetrahedral. Compounds of the type SnRR'RR' have been resolved into individual enantiomers.
The mixed organic-chloro compounds are also tetrahedral, although they form adducts with good Lewis bases such as pyridine. The fluoride tend to associate such that dimethyltin difluoride forms sheet-like polymers. The mixed organic tin hydrides, e.g. dialkyltin dihydride, are also generally monomeric. The parent member of this series, stannane (SnH4), is an unstable colourless gas.
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