
%0 Journal Article
%A Freeman, DJ 
%A Norris, RK 
%T Radical reactions of p-Nitrobenzylidene dichloride with lithium 2-nitropropan-2-ide. Consecutive S<sub>RN</sub>1 and E<sub>RC</sub>1 reactions
%J Australian Journal of Chemistry
%D 1976/12/01
%V 29
%N 12
%P 2631-2642
%K 
%R https://doi.org/10.1071/CH9762631
%U https://www.publish.csiro.au/paper/CH9762631 
%X The reaction of p-nitrobenzylidene dichloride with the lithium salt of 2-nitropropane gives initially the monosubstituted compound, p- NO2C6H4CH(Cl)CMe2NO2, by a radical-anion radical chain, SRN1 process. This compound then undergoes a radical-anion radical chain elimination reaction giving the styrene, p-NO2C6H4CH=CMe2, and the dimer of 2- nitropropane, Me2C(NO2)CMe2NO2. This latter reaction, which is designated ?ERC1?, also occurs in competition with an E2 reaction in the reaction of the methanesulphonate, p-NO2C6H4CH(OMs)CMe2NO2, with the 2- nitropropan-2-ide ion giving the above styrene and the enol methanesulphonate, p-NO2C6H4C(OMs)=CMe2, respectively. Catalytic, inhibition, and substituent effects are used to confirm the operation of these radical processes. 
