Birnbaum-Simonini reaction

What is Birnbaum-Simonini reaction?

The Birnbaum-Simonini reaction was initially described by Birnbaum in 1869 and later by Simonini in 1892. This chemical process involves heating a mixture of silver salts of carboxylic acids and iodine to produce esters.

Birnbaum-Simonini reaction - general reaction scheme
Birnbaum-Simonini reaction
Birnbaum-Simonini reaction - general reaction scheme
Birnbaum-Simonini reaction

Conversely, lactones are formed when the silver salts of dicarboxylic acids are heated with iodine. Since preparing and drying the silver salts is costly and inconvenient, this method has been improved by heating a combination of halogen with lead tetrasalts of carboxylic acids, which gives comparable yields. Additionally, this oxidative process of ester formation from metal salts of carboxylic acids has been modified to oxidize the carboxylic acids themselves, as well as their corresponding peracids and peranhydrides. Nevertheless, ester formation does not occur in the presence of an olefin.

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