P-toluenesulfonyl Azide

- Jun 12, 2018 -

    One of the applications of p-toluenesulfonyl azide (TsN _ 3) in organic chemistry is to act as a transfer reagent for azide functional groups. The reagents can introduce diazo functional groups into active methylene sites and react with olefins to form heterocyclic nitrogen compounds. Aliphatic diazo compounds can react with double bonds to form very important cyclopropane derivatives catalyzed by metal catalysts. Using TsN _ 3 in the presence of triethylamine can easily introduce diazo functional groups into the active methylene site. The reaction conditions are extremely simple, generally at room temperature or below room temperature can be placed to obtain a very good yield. Therefore, the experimental operation is also very safe. The functional groups of lipophilic methylene can be aldehydes, ketones, ester groups, cyanides, amides, nitro groups, aryl groups and so on, all of which are not affected in the reaction. Methylene with two electron-pulling groups is often the best substrate. When TsN _ 3 is co-heated with olefin, the heterocyclic nitrogen compounds can be easily formed, and the yield is very satisfactory. If appropriate metal catalysts are used, the reaction can be carried out at room temperature. Therefore, it can be expected that the reaction can be used to prepare chiral heterocyclic nitrogen compounds in the presence of chiral catalysts. It is a very interesting result that the reaction of TsN _ 3 with thiocarboxylic acid can easily produce corresponding amides at room temperature. However, the reaction of TsN _ 3 with monoamine and acetylene in the presence of CuI is worthy of attention. The reagent was prepared by in situ reaction of p-toluenesulfonyl chloride with sodium azide before use. The reaction conditions were simple and mild.

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