Nucleophilic substitution accompanying carbon-carbon bond cleavage assisted by a nitro group

作者:Nakaike Yumi; Taba Noriko; Itoh Shinobu; Tobe Yoshito; Nishiwaki Nagatoshi; Ariga Masahiro*
来源:Bulletin of the Chemical Society of Japan, 2007, 80(12): 2413-2417.
DOI:10.1246/bcsj.80.2413

摘要

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

  • 出版日期2007-12-15