Dibutyltin oxide, or dibutyloxotin, is an

organotin Organotin chemistry is the scientific study of the synthesis and properties of organotin compounds or stannanes, which are organometallic compounds containing tin–carbon bonds. The first organotin compound was diethyltin diiodide (), discove ...

compound with the

chemical formula 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, such as pare ...

(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 increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

.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 based on re-orientation of atomic nuclei with non-zero nuclear spins in an external magnetic f ...

and ¹¹⁹Sn

Mössbauer spectroscopy Mössbauer spectroscopy is a spectroscopic technique based on the Mössbauer effect. This effect, discovered by Rudolf Mössbauer (sometimes written "Moessbauer", German: "Mößbauer") in 1958, consists of the nearly recoil-free emission and a ...

Uses

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

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 al ...

acylation In chemistry, acylation is a broad class of chemical reactions in which an acyl group () is added to a substrate. The compound providing the acyl group is called the acylating agent. The substrate to be acylated and the product include the foll ...

, and

sulfonation In organic chemistry, aromatic sulfonation is a reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid () group. Together with nitration and chlorination, aromatic sulfonation is a widely used electrophilic aromatic substi ...

reactions for

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...

s and polyol. DBTO has been used in the regioselective

tosylation In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or TosIn this article, "Ts", unless otherwise stated, means tosyl, not tennessine.) is a univalent functional group with the chemical formula . It consists of a tolyl ...

(a specific type of sulfonation) of certain

polyols In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, thre ...

to selectively tosylate

primary alcohols A primary alcohol is an Alcohol (chemistry), alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group. In contrast, a secondary alcohol has a formula “–CHRO ...

and

exocyclic In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. Cyc ...

alcohols over more sterically-hindered alcohols. It also finds use as a

transesterification Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. Strong acids catalyze the r ...

catalyst. Dibutyltin compounds, such as dibutyltin dilaurate are widely used curing catalysts for the production of

silicone In Organosilicon chemistry, organosilicon and polymer chemistry, a silicone or polysiloxane is a polymer composed of repeating units of siloxane (, where R = Organyl group, organic group). They are typically colorless oils or elastomer, rubber ...

s and

polyurethane Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...

s.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