Electronic effects in the acid-promoted deprotection of N-2,4-dimethoxybenzyl maleimides

Abstract Cleavage of several 2,4-dimethoxybenzylmaleimides could be performed employing TFA in anisole. Electronic effects exemplified by varying the substitution present on the maleimide resulted in a variation in the rate of the deprotection. In contrast, 2,4-dimethoxybenzylsuccinimides were inert to the conditions.