179. Die Oxidation von 3-(1-Nitro-2-oxocycloalkyl)propanal

Article abstract of DOI:10.1002/hlca.19870700728

Oxidation of the title compound 1 with KMnO4 under neutral condiitons led to the corresponding acid 2, 5-(2,3,4,5-tetrahydro-2-nitro-5-oxo-2-furyl)pentanoic acid (4), and 4-oxononadioic acid (6).On the basis of experimental results the mechanism of the formation of 4 is discussed (Scheme 1).Oxidation of 1 with KMnO4 under basic conditions gave 6 which was transformed to (E)-4,5-dihydro-5-(2'-oxocyclopentyliden)furan-2(3H)-one (12) with benzene/TsOH (Scheme 3).In contrast to this result the corresponding 4-oxoheptandioic acid (22) yields 1,6-dioxaspiro<4.4>nonan-2,7-dione (23) only (Scheme 4).