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Organotin hydroxides and oxides are common products obtained from the hydrolysis of the corresponding organotin halides. Three types of organotin hydroxides and oxides are known, triorganotin hydroxides and oxides [R3SnOH and R3SnOSnR3], diorganotin hydroxides and oxides [R2Sn(OH)2 and R2SnO] and monoorganotin hydroxides and oxides. Triorganotin derivatives are the structurally simplest oxides and hydroxides.
Diorganotin hydroxides and oxides are structurally complex and exist as polymers except when the organic substituents are bulky. Mono organotin species are also structurally complex because of the occurrence of dehydration/hydration and aggregation. Organotin hydroxides and oxides are prepared from the corresponding halides under alkaline conditions. Alkyl iodides and benzyl bromides (RX) react with tributyltin oxide in the presence of fluoride ion source to give the corresponding ether R2O in excellent yield. Triorganotin oxides provide a method of deprotecting esters in aprotic solvents under neutral conditions.