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

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 equili...

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Bibliographic Details
Published in:	Bulletin of the Chemical Society of Japan Vol. 80; no. 12; pp. 2413 - 2417
Main Authors:	Nakaike, Yumi, Taba, Noriko, Itoh, Shinobu, Tobe, Yoshito, Nishiwaki, Nagatoshi, Ariga, Masahiro
Format:	Journal Article
Language:	English
Published:	Tokyo The Chemical Society of Japan 2007 Chemical Society of Japan
Online Access:	Get full text
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Summary:	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.
ISSN:	0009-2673 1348-0634
DOI:	10.1246/bcsj.80.2413