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Analysis of tributyltin oxide technology
Edit:Nantong Yutai Chemical Products Co., Ltd.   UpDate:2019-10-11

Even in the presence of excess reagent, tributyltin oxide -bromine can selectively oxidize sulfide to sulfoxide without further oxidation to sulfone. This reaction is very effective for the oxidation reaction of a long-chain hydrophobic alkyl sulfide, and the problem of poor solubility encountered when using periodic acid as an oxidizing agent is avoided (Formula 3). In addition, tributyltin oxide-bromine can also selectively oxidize the sulfenamide to the sulfinamide without oxidizing to the sulfonamide (Formula 4).

The mixture of tributyltin oxide-bromo-diphenylselenium is refluxed in a chloroform solvent to convert styrene into an α-keto selenide derivative (Formula 5).

Another feature of tributyltin oxide is that it activates oxygen and nitrogen, increases the nucleophilicity of oxygen and nitrogen, and makes them susceptible to ammonia sulfonation, carbamoylation, acylation, and alkylation. If the alcohol and sulfamoyl chloride are difficult to react, a tin-containing reagent can be first formed in the presence of tributyltin oxide. Then, the next reaction can be carried out without isolation to form an sulfonated product (Formula 6). This reaction is also widely used in the selective acylation reaction of a polyol (Formula 7).

This reaction can also be used in the activation reaction of nitrogen, such as the synthesis of pyridine nucleosides (Formula 8).

Tributyltin oxide also removes hydrogen sulfide. Tin compounds have sulfophilicity and are often used in the conversion of functional group compounds. For example, in the presence of tributyltin oxide, alkyl and arylsulfamides can be converted to nitriles (Formula 9).

In addition, tributyltin oxide can promote the progress of the hydrolysis reaction. In the presence of tributyltin oxide, hydrolysis proceeds readily to form the corresponding carboxylic acid derivative (Formula 10).

In the presence of silver p-toluenesulfonate, tributyltin oxide also promotes the hydrolysis of the primary alkyl iodide and the alkyl bromide to form the corresponding alcohol (Formula 11).

The palladium catalyst can catalyze the reaction of an enyne compound with tributyltin oxide to form a tin-benzene derivative at a high regioselectivity. This reaction not only achieves the arylation reaction, but also introduces a tin group on the aryl group, and further functionalizes the aryl group (Formula 12).

 

 


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