Helvetica Chimica Acta p. 1937 - 1943 (1987)
Update date:2022-08-04
Topics:
Zuercher, Alois
Hesse, Manfred
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).
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