Wharton fragmentation
The Wharton fragmentation is a name reaction in the field of organic chemistry and was 1961 by Peter S. Wharton observed. A breakdown or fragmentation of carbon chains with heterogeneous nucleophiles and leaving groups takes place.
Overview reaction
Wharton fragmentation is carried out in acidic , aqueous solution .
The radicals R stand for organic radicals and can differ from one another. The X can stand for halides or a hydroxide group, which are split off as a leaving group in the course of the reaction .
Possible mechanism
The following mechanism of Wharton fragmentation is explained in an acidic environment for 2,3,3,4-tetramethylpentane-2,4-diol, i.e. with methyl radicals as the radicals R and water as the leaving group.
The acid protonates the hydroxyl group of diol 1 , creating the oxonium ion 2 . Finally, by splitting off the leaving group and shifting the electrons, acetone , 2,3-dimethylbut-2-ene and water are formed .
application
Wharton fragmentation is used in the production of kainic acid .
literature
- László Kürti, Barbara Czakó: Strategic Applications of Named Reactions in Organic Synthesis , Elsevier Academic Press 2005, ISBN 978-0-12-429785-2 , pp. 480-481.
- CA Grob, PWSchiess: Applied chemistry , Society of German Chemists 1967, pp. 1-14