Dibutyltin oxide, or dibutyloxotin, is an organotin

Organotin

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, discovered by Edward Frankland in 1849...

 compound used in organic synthesis. Among many synthetic applications, it is particularly useful in regioselective alkylation

Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene . Alkylating agents are widely used in chemistry because the alkyl group is probably the most common group encountered in...

, acylation

Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....

, and sulfonation reactions for starting materials containing alcohol

Alcohol

In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

 functional groups.

Applications

Dibutyltin oxide (DBTO) may be used in the regioselective tosylation (a specific type of sulfonation) of certain polyols to selectively tosylate primary alcohols and exocyclic alcohols over more sterically-hindered alcohols: