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With strong bases, the positions 4 and 6 (the two CH 2-groups of the carbonyl group and the C-C double bond adjacent) are deprotonated. Cyclohexenone is an in-vitro catalyst for a relatively mild decarboxylation of alpha amino acids. [7] [8]
For example, the conjugate addition of methylamine to cyclohexen-2-one gives the compound 3-(N-methylamino)-cyclohexanone. Conjugated carbonyls react with hydrogen cyanide to 1,4-keto-nitriles. See hydrocyanation of unsaturated carbonyls. In the Nagata reaction the cyanide source is diethylaluminum cyanide.
Methylcyclohexanones are a group of three isomers: 2-methylcyclohexanone, 3-methylcyclohexanone, and 4-methylcyclohexanone. [1] They can be viewed as derivative of cyclohexanone. They can be prepared by oxidation of methylcyclohexane as well as partial hydrogenation of the corresponding cresols. All are colorless liquids. The 2- and 3-isomers ...
The archetypal Beckmann rearrangement [4] is the conversion of cyclohexanone to caprolactam via the oxime. Caprolactam is the feedstock in the production of Nylon 6. [5] The Beckmann solution consists of acetic acid, hydrochloric acid and acetic anhydride, and was widely used to catalyze the rearrangement.
Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: [5]. 2 C 6 H 12 + O 2 → 2 C 6 H 11 OH. This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid.
2 C 6 H 12 + O 2 → 2 C 6 H 11 OH. This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid, used to make nylon. The small cycloalkanes – in particular, cyclopropane – have a lower stability due to Baeyer strain and ring strain.
Here, the acid-catalyzed proton transfer first converts the cyclohexanone phenylhydrazone 1 to the intermediate 2. Subsequently, a heat-induced sigmatropic reaction occurs to produce 3, which is protonated and cyclizes into 4. Elimination of ammonia then leads to the final product, the tetrahydrocarbazole 5.
The Wichterle reaction is a variant of the Robinson annulation that replaces methyl vinyl ketone with 1,3-dichloro-cis-2-butene. This gives an example of using a different Michael acceptor from the typical α,β-unsaturated ketone. The 1,3-dichloro-cis-2-butene is employed to avoid undesirable polymerization or condensation during the Michael ...