Titanium(IV) enolates of 2-nitrocarboxylic esters and their oxidative chlorination : a convenient route to α-chloro-α-nitrocarboxylates

Bibliographic description

punktacja MEiN [2012 A]: 30

title:	Titanium(IV) enolates of 2-nitrocarboxylic esters and their oxidative chlorination : a convenient route to α-chloro-α-nitrocarboxylates
author:	Cież Dariusz , Kalinowska-Tłuścik Justyna
journal title:	Synlett
volume:	23
issue:	2
date of publication :	2012
pages:	267-271
ISSN:	0936-5214
eISSN:	1437-2096
DOI:	10.1055/s-0031-1290081
language:	English
journal language:	English
abstract in English:	A new method for the synthesis of 2-chloro-2-nitrocarboxylic esters from 2-nitrocarboxylates is described. The procedure consists of the oxidative chlorination of titanium(IV) enolates of 2-nitro esters in the presence of ammonium nitrate. Esters of 2-chloro-2-nitrocarboxylic acids are formed in very good to quantitative yields. Application of this method for the chlorination of $\alpha$,$\alpha$′-dinitrodicarboxylates leads to $\alpha$,$\alpha$′-dichloro-$\alpha$,$\alpha$′-dinitrocarboxylic esters with high meso-diastereoselectivity. The absence of ammonium nitrate from the reaction mixture affects the reduction of nitro groups and leads to partial transformation of 2-nitrocarboxylic esters into 2-(hydroxyimino)carboxylates.
keywords in English:	oxidative chlorination, diastereoselectivity, titanium enolates, esters, transition states
departmental parameterization:	30
affiliation:	Wydział Chemii : Zakład Krystalochemii i Krystalofizyki, Wydział Chemii : Zakład Chemii Organicznej
type:	journal article
subtype:	academic paper

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