Chemistry of dinitroacetonitrile—II (original) (raw)
Addition of dinitroacetonitrile to carbonyl conjugated unsaturated systems was a generally successful reaction for the preparation of Michael adducts. The expected products were obtained with methyl acrylate, acrylamide, acrolein, butenone, methylene-bis-acrylamide, and N,N',N"-triacrylylperhydro-s-triazine. Acrylic acid gave three products: the normal adduct, the corresponding carbamyl derivative and its cyclic imide. Dinitrocyanoethanol was easily prepared by reaction of dinitroacetonitrile with formaldehyde and the acetate, trifluoroacetate, acrylate and methacrylate esters of this alcohol were characterized. Esterification with 3,5-dinitrobenzoylchloride, fumaryl chloride and succinyl chloride gave liquid esters which could not be purified. N-(2,2-Dinitro-2-cyanoethyl)amides could be prepared in relatively general fashion as the products of reaction of dinitroacetonitrile with N-methylolamides. The corresponding acetyl, benzoyl, acrylyl, methacrylyl and bis-urea derivatives are described. These compounds were sensitive toward hydrolysis. Alkylation of dinitroacetonitrile and its salts to give identifiable products was not generally successful. As special cases the C-allyl, O-methyl, C-t-butyl and N-t-butyl derivatives could be prepared and were characterized.
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