Simonini reaction
The Simonini reaction is a name reaction in organic chemistry that was first described by Angelo Simonini in 1892 and named after him. In the reaction, aliphatic esters are prepared by decarboxylating the silver salts of carboxylic acids in the presence of iodine in an inert solvent . It is closely related to the Hunsdieker reaction and is also called the extension of this reaction.
Overview reaction
In the Simonini reaction, two equivalents of an aliphatic silver carboxylate are reacted with iodine to form an aliphatic ester. Carbon dioxide and two equivalents of silver iodide are produced as by-products .
Reaction mechanism
In contrast to the Hunsdiecker reaction, the Simonini reaction follows an ionic mechanism. First, the alkyl iodide 2 is formed from the silver carboxylate 1 with iodine with the elimination of carbon dioxide . In the presence of the second equivalent of silver carboxylate, a nucleophilic substitution takes place , which leads to the formation of the ester 3 .
Practical meaning
The Simonini reaction is of little practical importance, since the procurement of the required silver carboxylates is expensive and the preparation of the substances is complex. This aspect and the poor atom economy due to the formation of stoichiometric amounts of several waste materials mean that other routes for the synthesis of esters are preferred.
Individual evidence
- ↑ a b c d Zerong Wang: Simonini Reaction . In: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 2600-2602 , doi : 10.1002 / 9780470638859.conrr587 .
- ↑ Entry on Simonini reaction. In: Römpp Online . Georg Thieme Verlag, accessed on December 14, 2018.
- ↑ a b Jie Jack Li, EJ Corey: Name Reactions for Functional Group Transformations . John Wiley & Sons, Inc., Hoboken, New Jersey 2007, ISBN 978-0-470-17651-1 , pp. 623 , doi : 10.1002 / 9780470176511 .