Tributyltin oxide
[English name] bis (tri-n-butyltin) oxide
[molecular formula] c24h54osn2
[molecular weight] 596.20
[CAS No.] 56-35-9
[preparation and alias] btbto, TBTO, bisttributyltin oxide, bis (tributyltin) oxide, bis (tributyltin oxide).
[physical properties] colorless liquid, BP 180 ℃ / 2.0 mmHg, D 1.170g/cm3. Soluble in most organic solvents, insoluble in water.
[preparation and commodity] international large reagent companies have sales. It can also be prepared according to the following method: Tetrabutyltin is formed by the reaction of anhydrous tin tetrachloride with butyl magnesium bromide, and then reacts with tin tetrachloride to form tributyltin chloride, and finally reacts with potassium hydroxide to obtain tributyltin oxide.
[precautions] it shall be placed in a safe place to avoid direct contact. It is generally used in dry anhydrous system and operated in ventilation shed.
In the presence of bromine reagent, tributyltin oxide can promote the oxidation of propylene alcohol, benzyl alcohol, secondary alcohol and sulfide. This method is very practical and can selectively oxidize secondary alcohols into ketones in the presence of primary alcohols.
In the presence of NBS, tributyltin oxide can also highly selectively oxidize secondary alcohols to ketones, and the reaction occurs on secondary alcohols with less steric hindrance.
Even in the presence of excess reagent, tributyltin oxide bromine can selectively oxidize sulfide to sulfoxide without excessive oxidation to sulfone. This reaction is very effective for the oxidation reaction containing long-chain hydrophobic alkyl sulfide, and avoids the problem of poor solubility when periodic acid is used as an oxidant. Tributyltin oxide bromine can also selectively oxidize hyposulfonamides to sulfinamides without over oxidation to sulfonamides.
By refluxing the mixture of tributyltin oxide bromine diphenyl diselenide in chloroform, styrene can be converted into α- Ketone selenium derivative.
Another characteristic of tributyltin oxide is that it can activate oxygen and nitrogen, increase the nucleophilicity of oxygen and nitrogen, and make them easier to carry out sulfation, formylation, acylation and alkylation reactions. If it is difficult for alcohol to react with sulfamoyl chloride, tin containing reagent can be formed first in the presence of tributyltin oxide. Then, the next step reaction can be carried out without separation to form the sulfated product. This reaction has also been widely used in the selective acylation of polyols Yes.
This reaction can also be used in the activation reaction of nitrogen, such as the synthesis of pyridine nucleoside.
Tributyltin oxide can also remove hydrogen sulfide. Tin compounds are sulfophilic and are often used in the conversion of functional compounds. For example, in the presence of tributyltin oxide, alkyl and aryl thioamides can be converted into nitriles.
Tributyltin oxide can also promote the hydrolysis of esters. In the presence of tributyltin oxide, carboxylic acid esters hydrolyze to form corresponding carboxylic acids.
In the presence of silver p-methylbenzenesulfonate, tributyltin oxide can also promote the hydrolysis reaction of primary iodide and bromine to produce corresponding alcohols.
Palladium catalysts can catalyze the reaction of alkynes with tributyltin oxide to produce tin substituted benzene derivatives with high regioselectivity. This reaction not only realizes the C-arylation reaction, but also introduces a Tin Group on the aryl group, which can further functionalize the aryl group.
