Dibutyltin oxide, or dibutyloxotin, is an

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 ...

compound with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

(C₄H₉)₂SnO. It is a colorless solid that, when pure, is insoluble in organic solvents. It is used as a reagent and a

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

.Davies, Alwyn G. "Organotin Chemistry", 2nd Edition, 2004, Wiley-VCH: Weinheim. .

Structure

The structure of diorganotin oxides depends on the size of the organic groups. For smaller substituents, the materials are assumed to be polymeric with five-coordinate Sn centers and 3-coordinate oxide centers. The result is a net of interconnected four-membered Sn₂O₂ and eight-membered Sn₄O₄ rings. The presence of pentacoordinate Sn centers is deduced from ¹¹⁹Sn

NMR spectroscopy Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a spectroscopic technique to observe local magnetic fields around atomic nuclei. The sample is placed in a magnetic fiel ...

and ¹¹⁹Sn Mössbauer spectroscopy.

Uses

In organic synthesis, among its many applications, it is particularly useful in directing regioselective O-

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 (or their equivalents). Alkylating agents are reagents for effecting ...

, acylation, and sulfonation reactions for

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is e ...

s and polyol. DBTO has been used in the regioselective

tosylation In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula –. It consists of a tolyl group, –, joined to a sulfonyl group, ––, with the open valence on s ...

(a specific type of sulfonation) of certain polyols to selectively tosylate primary alcohols and exocyclic alcohols over more sterically-hindered alcohols. It also finds use as a transesterification catalyst. Dibutyltin compounds, such as

dibutyltin dilaurate Dibutyltin dilaurate (abbreviated DBTDL), also called dibutyltindilaurate or butynorate, is an organotin compound that is used as a catalyst. It is a colourless oily liquid. In terms of its structure, the molecule consists of two laurate groups a ...

are widely used curing catalysts for the production of

silicone A silicone or polysiloxane is a polymer made up of siloxane (−R2Si−O−SiR2−, where R = organic group). They are typically colorless oils or rubber-like substances. Silicones are used in sealants, adhesives, lubricants, medicine, cooking ...

s and polyurethanes.Jorge Cervantes1, Ramón Zárraga, Carmen Salazar-Hernández "Organotin catalysts in Organosilicon Chemistry" Appl. Organometal. Chem. 2012, volume 26, 157–163. {{doi, 10.1002/aoc.2832

References

Organotin compounds Four-membered rings Eight-membered rings Two-dimensional nanomaterials Tin(IV) compounds Butyl compounds

Structure

Uses

See also

References