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Journal of Applied Chemistry
Volume 2013 (2013), Article ID 415639, 3 pages
Research Article

Synthesis and Spectral Characterization of Novel Spiroindan-1,3-Dione: A Diels Alder Adduct

Department of Chemistry, University of Kashmir, Srinagar, 190006 Jammu and Kashmir, India

Received 25 August 2013; Revised 24 November 2013; Accepted 8 December 2013

Academic Editor: Luqman Chuah Abdullah

Copyright © 2013 N. D. Zargar and K. Z. Khan. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


DMSO/Ac2O reagent converts 1,3-indandione (1) to an unusual dimer 1H,1′H-2,2′-biindene-1,1′,3,3′(2H,2′H) tetrone and a dimeric condensation product along with an ylide (1a) at room temperature. This reagent also brings about oxidation of secondary alcohols to corresponding ketones, methyl thiomethylation, and N-hydroxymethylation in phthalimide and converts 4-hydroxycoumarins and dicoumarol to different oxidative and degradation products under varying conditions. However, when 1,3-indandione was refluxed with DMSO/Ac2O reagent at 150°C, it afforded a novel compound, 2-spiroindan 1,3-dione (2), a Diels Alder Adduct, analogous to (3) obtained upon treatment of 1,3-indandione with formaldehyde in presence of primary amines.