Hooker reaction

Hooker oxidation reaction is a name of organic chemistry. It was named after the English chemist Samuel Cox Hooker ( 1964-1935 ). Using this reaction, it is possible ( or alkenyl ) -1,4- benzoquinone to exchange the hydroxyl and alkyl ( alkenyl ) group within a 2 -hydroxy-3 -alkyl, the latter being less after the reaction, a methyl group, contains.

Overview reaction

The reaction may be performed in place of potassium permanganate as the oxidizing agent with a combination of hydrogen peroxide and sodium carbonate.

Mechanism

The R1 radical mechanism explained in the following the orientation of the molecule and indicates that the hydroxyl group and the alkyl ( alkenyl ) group actually swap positions.

First, the hydroxy group is deprotonated molecule 1 and the resulting anion 2, a permanganate ( 3) approaches to. The molecules 4, 5 and 6 show how the permanganate ion, the carbon atoms to which were located at the beginning of R2 and the hydroxy group is oxidized and himself the manganese (IV ) oxide is reduced. Now, a hydroxide ion one of the hydrogen atoms 7, which are in α -position to the R2 radical and a carbonyl hydroxide. The following is an intramolecular nucleophilic attack of the carbanion 7 to the carbonyl carbon atom, and thus the closure of a six-membered ring 8 to cleave a formate anion, the molecule arises 9 after the movement of the electrons 10, and subsequent acidic (H ) workup with formed product 11 by the hydroxy group and the now shortened by one methylene group alkyl or alkenyl group have swapped positions.