Dimethyl sulphoxide as a reagent brings about N-methylthiomethylation and N,N/-methylthiomethylation in substituted barbituric acids. It converts 4-acetoxy coumarins to corresponding ylides and brings about methylene insertion in 1,6-naphtharidenes at reflux temperature.DMSO activated by trifluoro-aceticanhydride brings about formation of mono, bis and tris-sulphonic substituted derivatives when interacted with cyclo pentadiene and trimethylsilyl cyclopentadiene.This reagent converts 3-Nitro-4-hydroxy coumarins to salicylic acid in dichloromethane at low temperature.DMSO-acetic anhydride reagent converts enols to sulphur ylides, introduces methylthiomethyl group into phenols and oxidizes secondary alcohols to corresponding ketones. It brings about oxidative rearrangement in polyporic acid and converts 4-hydroxy coumarins and its 3-substituted derivatives into a wide range of products under different conditions.DMSO-SO3 pyridine complex in presence of triethyl amine oxidizes cis-diols to corresponding quinones.DMSO-activated by N-bromosuccinimide brings about methylation of alcohols and converts diols to their corresponding methylene-acetals.
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.
Dimethyl sulphoxide activated by acetic-anhydride introduces methylthiomethyl group into phenols,oxidises certain medicinally useful secondary alcohols to their corresponding ketones and brings about oxidative rearrangements in different substrates.It converts 4-hydroxy coumarins and dicoumarols,under varying conditions,to a variety of products of both pharmaceutical and mechanistic interest. When1,3-indandione (1) was interacted with this versatile reagent at water bath temperature,it afforded an ylide (2) and an oxidative cyclisation product (3).However,its interaction with Ar –CH = (CN)R,leads to the formation of a mechanistically interesting compound,indeno[1,2-b]-4H pyran(4). DMSO alone has been used as a reagent and yields a number of products of mechanistic interest with different substrates.When 1,3-indandione (1) was refluxed with DMSO alone at elevated temperature,it results the formation of poly(methylene-bis) 1,3-indandione(5) involving methylene group insertion between different 1,3-indandione moieties.Methylene insertion has also been observed when 1,3-indandione (1) was condensed with formaldehyde in presence of alkali carbonates or primary amines to yield (6)and(7) respectively.
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