F. M. Abdelrazek, N. Metwally, N. Kassab
Nov 1, 2014
Citations
0
Influential Citations
4
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Cyclopentanone reacts with malononitrile catalyzed by piperidine or sodium acetate to afford under any case cyclopentylidenemalononitrile dimer: 5-aminospiro-[2,6,7,7a-tetrahydroindene-7,1′-cyclopentane]-4,6,6-tricarbonitrile (7) as the sole product. Contrary to this behavior, cyclohexanone reacts with malononitrile catalyzed by piperidine to afford the analogous cyclohexylidenemalononitrile dimer: 2-aminospiro-[3,4,5,6,7,4a-hexahydronaphthalene-4,1′-cyclohexane]-1,3,3-tricarbonitrile (11); whereas when the reaction is catalyzed by sodium acetate, it afforded 9,10-diaza-8,11-dioxo-tricyclo-[4.3.3.01,6]-dodecane-7,12-dicarbonitrile (12). The structures of these products were established on the basis of their elemental analysis and spectral data, and plausible mechanism has been postulated to account for their formation. X-ray crystallography was carried out as a further evidence for structures 7 and 12.