40357-77-5Relevant academic research and scientific papers
SYNTHESIS AND REARRANGEMENT OF IMIDIC ANHYDRIDES DERIVED FROM DICARBOXYLIC ACID DIAMIDES
Mazurkiewicz, Roman
, p. 831 - 838 (2007/10/02)
Imidic anhydrides (1), a new class of imidic acid derivatives, were readily obtained in high yields from the reaction of N,N'-disubstituted diamides of dicarboxylic acids with Ph3PBr2 in CH2Cl2 in the presence of triethylamine as HBr captor.Imidic anhydrides, when treated with an excess of HCl (HCl/1 ratio of 1.5:1) in CH2ClCH2Cl, rearrange to the isomeric iminolactams 2 in high yields, though at very different rates.In the presence of merely 0.5 mol of HCl per mol of the imidic anhydride 1b, the required rearrangement time is several hundred times longer.This and other observation suggest that diprotonation of the imidic anhydrides is a necessary condition of rearrangement.
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.
