Abstract3-exo-Hydroxymethyl-5,5,6-trimethylbicyclo[2.2.1]heptan-2-one was prepared by treatment of isocamphanone with Paraform in the presence of alkali in DMF. The product reacts with acetonitrile in the presence of sulfuric acid (Ritter reaction) to form a mixture of 2-(acetylamino)-3-(acetylaminomethyl)-5,5,6-trimethylbicyclo[2.2.1]hept-2-ene and 2,2-bis(acetylamino)-3-(acetylaminomethyl)-5,5,6-trimethylbicyclo[2.2.1]heptane in a ∼1:1 ratio. Attempted hydroxymethylation of isocamphanone in DMSO gave bis(isocamphanon-3-endo-yl)methane.

3-exo-Hydroxymethyl-5,5,6-trimethylbicyclo[2.2.1]heptan-2-one is a novel synthesis method for preparing complex organic compounds with potential applications in organic synthesis and catalysis.

Paper

Synthesis and Ritter Reaction of 3-exo-Hydroxymethyl-5,5,6-trimethylbicyclo[2.2.1]heptan-2-one

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