
%0 Journal Article
%A Norris, RK 
%A Smyth-King, RJ 
%T Reaction of 2-Nitropropan-2-ide Ion with <I>m</I>-Nitrobenzylidene Dibromide and Dichloride
%J Australian Journal of Chemistry
%D 1979/09/01
%V 32
%N 9
%P 1949-1960
%K 
%R https://doi.org/10.1071/CH9791949
%U https://www.publish.csiro.au/paper/CH9791949 
%X The reactions of m-nitrobenzylidene dichloride and dibromide with lithium 2-nitropropan-2-ide in dimethyl sulfoxide give a complex mixture of products (unlike the p-nitro isomers), which include: 1-chloro(bromo)-2-methyl-2-nitro-1-m-nitrophenylpropane and &#946;,&#946;-dimethyl-m-nitrostyrene, formed by SRN1 and ERC1 processes; 1-(1-methyl-1-nitroethyl)-2(and 4)-(2-methylprop-1-enyl)-4(and 2)- nitrobenzene, formed by nucleophilic ring attack; and acetone O-m-nitrobenzoyloxime and m-nitrobenzoic acid formed by radical and/or ionic processes. Several routes to 2-methyl-2-nitro-1-m-nitrophenylpropan-1-one, proposed as an intermediate leading to the above oxime ester, are proposed. Inhibitory and catalytic effects on these reactions are discussed. 
