α-nitrocycloalkanones as a new source for the one-pot synthesis of functionalized 1,4-diketones, γ-oxoaldehydes, γ-ketoesters, and methyl ω- oxoalkanoates

Article abstract of DOI:10.1016/S0040-4020(98)00391-3

Methyl ω-oxoalkanoates were obtained via ring cleavage of α- nitrocycloakanones by refluxing these compounds in a methanolic solution of KOH, then treating the obtained mixture, at 0 °C, with an aqueous solution of KMnO₄/MgSO₄. 1,4-Diketones, γ-oxoaldehydes, and γ-ketoesters were also prepared by conjugated addition of α-nitrocycloakanones to the appropriate conjugated enones, in MeOH/Ph₃P, then by, in situ, ring cleavage-Nef reaction following the above conditions.