Coupling of Enolates of Phenones with 2-Chloro-2-nitropropane

Article abstract of DOI:10.1021/jo00349a012

Lithium enolates of acetophenone, α-methoxyacetophenone, propiophenone, meta- or para-substituted propiophenones, butyrophenone, isovalerophenone, 1-phenyl-1-hexanone, 1-indanone, 1-tetralone, or 1-benzosuberone react with 2-chloro-2-nitropropane in THF by free radical chain processes to produce ArCOCH(CMe2NO2)R or ArCOC(R)=CMe2 and when R <*> H the product of oxidative dimerization, 2.The enolate anion of deoxybenzoin yields in a free radical chain process only the dimerization product.