Metal-free Homocoupling of 2,2´-(Arylmethylene)-bis(3-hydroxy-5,5- dimethylcyclohex-2-enone) Mediated by N-methylhydroxylamine

Author(s): Jamal Lasri.

Journal Name: Letters in Organic Chemistry

Volume 10 , Issue 7 , 2013

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The reaction of 5,5-dimethylcyclohexane-1,3-dione with an acyclic nitrone in DMF or acetone affords a 1:1 mixture of dimer 2,2´-(arylmethylene)-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) and tetramer 2,2',2'',2'''-(1,2- diarylethane-1,1,2,2-tetrayl)tetrakis(3-hydroxy-5,5-dimethyl-cyclohex-2-enone). This unprecedented type of metal-free homocoupling of two molecules of the dimer to furnish the tetramer is believed to proceed via an oxidation/reduction process involving N-methylhydroxylamine.

Keywords: Acyclic nitrones, C-C bond formation, 5, 5-dimethylcyclohexane-1, 3-dione, N-methylhydroxylamine, oxidative coupling.

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Article Details

Year: 2013
Page: [482 - 489]
Pages: 8
DOI: 10.2174/15701786113109990013
Price: $65

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