ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Oxidation of 3-(1-Nitro-2-oxocycloalkyl)propanalOxidation of the title compound 1 with KMnO4 under neutral conditions 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).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700728
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