Nucleophilic Substitution Accompanying Carbon-Carbon Bond Cleavage Assisted by a Nitro Group

摘要

A 2-nitrated 3-oxoester reacted with amines or alcohols to afford unsymmetrical malonic acid derivatives as a result of nucleophilic substitution accompanying C-C bond cleavage.The 2-nitrated 3-oxoester easily formed ammonium sate with amines.When the armners liberated from the salt under equilibrium,nucleophilic amine and electrophilic keto ester locate close to each other This ultimate pair effect causes a pseudo intramolecular reaction to occur,giving rise to effective substitution under mild conditions.