Examination of the mechanism of base hydrolyses of N-(p-nitrophenoxymethyl)-substituted imides

摘要

The N-(CH_2PR)-phthalimide and N-(CH_2PR)-saccharin series of compounds (PR chemical bounds photographic reagent) are of interest for their utility in color instant photographic systems. The acidic p-nitrophenol is a good model for the released photographic reagents. The release of p-nitrophenol from N-(p-nitrophenoxymethyl)phthalimide in base has been proposed by others to proceed via direct S_N2 displacement at the methylene carbon. We have reexamined the mechanistic aspects of base hydrolysis of this molecule and o ther substituted imides in mixed aqueous/organic solutions. Our findings and the new mechanims they suggest is described.