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In recent times the catalytic oxidation of cyclohexene by (immobilized) metalloporphyrin complexes has been found to be an efficient way. [7] [8] In laboratory, cyclohexene oxide can also be prepared by reacting cyclohexene with magnesium monoperoxyphthalate (MMPP) in a mixture of isopropanol and water as solvent at room temperature. [9]
Potassium permanganate is often used as the oxidant for dihydroxylation; however, due to its poor solubility in organic solvent, a phase-transfer catalyst (such as benzyltriethylammonium chloride, TEBACl) is also added to increase the number of substrates for dihydroxylation. [18] Mild conditions are required to avoid over-oxidation.
The chemical chameleon reaction shows the process in reverse, by reducing violet potassium permanganate first to green potassium manganate and eventually to brown manganese dioxide: [1] [2] [5] KMnO 4 (violet) → K 2 MnO 4 (green) → MnO 2 (brown/yellow suspension) Blue potassium hypomanganate may also form as an intermediate. [6]
Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene. [6] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. [7] Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam. [8] The oxidative cleavage of cyclohexene gives adipic acid.
In general Sharpless asymmetric dihydroxylation favors oxidation of the more electron-rich alkene (scheme 1). [22] SAD scheme 1. In this example SAD gives the diol of the alkene closest to the (electron-withdrawing) para-methoxybenzoyl group, albeit in low yield.
Addition of concentrated sulfuric acid to potassium permanganate gives Mn 2 O 7. [76] Although no reaction may be apparent, the vapor over the mixture will ignite paper impregnated with alcohol. Potassium permanganate and sulfuric acid react to produce some ozone, which has a high oxidizing power and rapidly oxidizes the alcohol, causing it to ...
The Lemieux–Johnson or Malaprade–Lemieux–Johnson oxidation is a chemical reaction in which an olefin undergoes oxidative cleavage to form two aldehyde or ketone units. The reaction is named after its inventors, Raymond Urgel Lemieux and William Summer Johnson , who published it in 1956. [ 1 ]
Aliquat 336 is used as a phase transfer catalyst, [2] including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid. [3] This reaction is an example of green chemistry, as it is more environmentally friendly than the traditional method of oxidizing cyclohexanol or cyclohexanone with nitric acid or potassium permanganate, which produce hazardous wastes.