98143-39-6Relevant academic research and scientific papers
Titanium(IV) enolates of 2-nitrocarboxylic esters and their oxidative chlorinationa convenient route to α-chloro-α-nitrocarboxylates
Ciez, Dariusz,Kalinowska-T?us?cik, Justyna
supporting information; experimental part, p. 267 - 271 (2012/03/11)
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 α,α′-dinitrodicarboxylates leads to α,α′- dichloro-α,α′-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. Georg Thieme Verlag Stuttgart - New York.
