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

Yumi Nakaike, Noriko Taba, Shinobu Itoh, Tobe Yoshito, Nagatoshi Nishiwaki*, Masahiro Ariga

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

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 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.

Original languageEnglish
Pages (from-to)2413-2417
Number of pages5
JournalBulletin of the Chemical Society of Japan
Volume80
Issue number12
DOIs
StatePublished - 1 Dec 2007

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