Organotin chemistry
Di- and especially tri-organotin halides, e.g. tributyltin chloride, exhibit toxicities approaching that of hydrogen cyanide.The distannoxanes exist as dimers with the formula [R2SnX]2O2 wherein the X groups (e.g., chloride –Cl, hydroxide –OH, carboxylate RCO2−) can be terminal or bridging (see Table).Numerous examples of hypercoordinated compounds are provided by the organotin oxides and associated carboxylates and related pseudohalide derivatives.The all-organic penta- and hexaorganostannates(IV) have even been characterized,[7] while in the subsequent year a six-coordinated tetraorganotin compound was reported.For example, tributyltin hydride (tris(n-butyl)stannane) serves as a useful source of "hydrogen atoms" because of the stability of the tributytin radical.Indeed, compounds with the formula R2Sn=SnR2, called distannenes or distannylenes, which are tin analogues of ethylenes R2C=CR2, are known for certain organic substituents.Such species reversibly dimerize to the distannylene upon crystallization:[12] Stannenes, compounds with tin-carbon double bonds, are exemplified by derivatives of stannabenzene.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-type cluster and a prismane.However, such reactions are temperamental, typically requiring a very weak carbon-halogen bond (e.g. an alkyl iodide or an allyl halide) or crown-complexed alkali metal salt catalyst.[19] Alternatively, stannides attack organic electrophiles to give organostannanes, e.g.:[2]: 49 Important reactions, discussed above, usually focus on organotin halides and pseudohalides with nucleophiles.Diorganotin carboxylates, e.g., dibutyltin dilaurate, are used as catalysts for the formation of polyurethanes, for vulcanization of silicones, and transesterification.[2] n-Butyltin trichloride is used in the production of tin dioxide layers on glass bottles by chemical vapor deposition.[2] Tributyltin compounds were once widely used as marine anti-biofouling agents to improve the efficiency of ocean-going ships.Concerns over toxicity[22] of these compounds (some reports describe biological effects to marine life at a concentration of 1 nanogram per liter) led to a worldwide ban by the International Maritime Organization.
trimethyltin chlorideorganometallic compoundscarbonEdward FranklandGrignard reagentspyridinetributyltin chloridehydrogen cyanidestannaneTributyltin hydrideStannoxaneethersalcoholsacaricidecyhexatingeminal diolsketonestrimersdimerschloridehydroxidecarboxylatecoordinatedelectronegativebipyridinelithiumtrigonal bipyramidal structurebond lengthsapicalcarbocationstetrel radicalpolystannanesalkenesdouble bondcarbon groupethylenestrigonal planarpyramidalMonomericcarbenesdimerizestannabenzeneStannolesstructural analogscyclopentadienecubane-type clusterprismaneethyl grouptriple bondalkynesGrignard reagenttin tetrachlorideredistribution reactionsorganoaluminium compoundsiodidecrown-complexedLewis acidsionic solventlithium aluminium hydrideWurtz-likealkyl sodium compoundsHydrostannylationstannideshalidespseudohalidesnucleophileshydrolyzeacetylidesorganostannane additionnucleophilic additionallenylpropargylstannanesaldehydesimineshydrogen gasorganic synthesisStille reactioncoupling techniquesp2-hybridizedorganic halidesvinyl chloridepalladiumradical chemistryradical cyclizationsBarton–McCombie deoxygenationBarton decarboxylationpolyvinyl chloridehydrogen chloridedibutyltin dilauratepolyurethanesvulcanizationsiliconestransesterificationn-Butyltin trichloridetin dioxidechemical vapor depositionTributyltinsbiocidesmiticidesacaricidesTributyltin oxidewood preservativebiofoulingnanogramInternational Maritime OrganizationdichlorooctylisothiazolinoneTetrabutyltinwood preservationTriphenyltin acetateinsecticidefungicideTriphenyltin chlorideTriphenyltin hydroxidespider mitesmiticideTetraethyltinboiling pointphytotoxicbactericidesfungicidesanti-fouling paintTributyltin azideCarbastannatranesUllmann's Encyclopedia of Industrial ChemistryJ. Am. Chem. Soc.Organometallics