13131-59-4Relevant articles and documents
Synthesis of Norbornanones with a Geminal Dimethyl Group
Buchbauer, Gerhard,Dworan, Erich
, p. 1165 - 1174 (2007/10/02)
The synthesis of gem-dimethylnorbornanones is described.One synthetic pathway after a Diels-Alder reaction involves the transformation of the nitro group into the oxo group with subsequent methylation into the geminal dimethyl product.A shorter way by -cycloaddition of cyclopentadiene with a suitable dimethylated dienophile (e.g. 2-methyl-1-nitropropene) failed, probably by steric hindrance of the dienophile. 7-Oxanorbornanones with a gem -dimethyl group could not be prepared.A second synthetic approach to gem-dimethylnorbornanones is opened by Lewis acid catalyzed rearrangement of cyclohexenylcarbaldehydes. - Keywords: Camphenilone; Diels-Alder reaction; Homonorbornanone; α-Methylation of carbonyls; Nef-reaction; Norepifenchone