
%0 Journal Article
%A Norris, RK 
%A Randles, D 
%T Nucleophilic Substitution Reactions of Tetrabutylammonium <I>aci</I>-Nitronates with p-Substituted Nitrobenzenes
%J Australian Journal of Chemistry
%D 1979/11/01
%V 32
%N 11
%P 2413-2422
%K 
%R https://doi.org/10.1071/CH9792413
%U https://www.publish.csiro.au/paper/CH9792413 
%X The reactions of tetrabutylammonium aci-nitronates with p-dinitrobenzene in dimethyl sulfoxide, benzene or acetone proceed far more rapidly than the reactions of the corresponding lithium salts and give, in unhindered cases, good yields of C-arylates, e.g. p-(1-methyl-1-nitroethyl)nitrobenzene (in 73-89% yields) and p-nitro(l,3,3-trimethyl-1-nitrobuty1)benene (in 70% yield). With more sterically hindered nitronates, O-arylation increases, giving phenols and ketoxime O-p-nitrophenyl ethers, presumably derived from the novel, intermediate p-nitrophenyl aci-nitronate esters. aci-Nitronate ions with more than two &#946;-methyl groups gave no C-arylation. Similar results were obtained with p-fluoronitrobenzene and p-nitrobenzonitrile, A mechanism for the conversion of the intermediate aci-nitronate esters into the ketoxime ethers is proposed. 
