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INTRAMOLECULAR N- AND O-IMIDOYLATION OF THE CARBOXAMIDE GROUP
Mazurkiewicz, Roman
, p. 115 - 125 (2007/10/02)
N,N'-Disubstituted diamides of dicarboxylic acids have been found to react with Ph3PBr2 to form intramolecular N-imidoylation products (5- or 6-iminolactams); only from N,N'-diphenylmaleamide the O-imidoylation product (N,N'-diphenylmaleimidic anhydride 6) was obtained.The imidic anhydride 6 in CH2Cl2 solution, in the presence of HBr undergoes a rearrangement to the respective iminolactam.Possible mechanisms of these reactions are discussed.Both the 13C NMR and 1H NMR spectra indicated the presence of Z,Z and Z,E-isomers in the imidic anhydride 6.
