124082-83-3Relevant 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.
