Fétizon oxidation
The Fétizon oxidation is a name reaction in organic chemistry, which was first introduced in 1968 by Marcel Fétizon and Michel Golfier and named after Fétizon. It describes a mild oxidation of alcohols to carbonyl compounds.
Overview reaction
The reaction uses silver carbonate on kieselguhr as an oxidizing agent. In the case of silver carbonate on kieselguhr, this is also referred to as the Fétizon reagent. This is a milder oxidizing agent than, for example, silver oxide .
1,4- diols , 1,5-diols and lactols are frequently oxidized to lactones . In this case, the term Fétizon cyclization is also used.
Reaction mechanism
At the beginning there is a nucleophilic attack 1 on one of the silver atoms of the silver carbonate, whereby the attacking oxygen atom receives a positive charge and the releasing oxygen atom a negative charge. Then the positively charged oxygen atom is deprotonated by the negatively charged oxygen atom 2 , whereby both are again neutrally charged. This process is repeated with the attack on the silver atom and the subsequent deprotonation. The resulting carbonic acid breaks down into water and carbon dioxide , while at the same time the silver atoms are split off 3 and the end product is created.
modification
This reaction was modified so that water can be removed via azeotropic distillation with toluene .
application
The reaction has a wide range of uses from the production of aldehydes , ketones , lactones , quinones and quinoxalines .
Individual evidence
- ↑ a b c d e Zerong Wang: Fétizon Oxidation . In: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 1055-1059 , doi : 10.1002 / 9780470638859.conrr230 .
- ^ Gabriel Tojo, Marcos Fernández: Fétizon's Reagent: Silver Carbonate on Celite® . In: Oxidation of Alcohols to Aldehydes and Ketones . Springer-Verlag, New York 2006, ISBN 978-0-387-23607-0 , pp. 281-288 , doi : 10.1007 / 0-387-25725-x_7 .