
%0 Journal Article
%A Norris, RK 
%A Randles, D 
%T The correlation of regiochemistry with structure in the S<sub>RN</sub>1 reaction of <I>aci</I>-nitronates with <I>p</I>-nitrobenzylic substrates
%J Australian Journal of Chemistry
%D 1982/08/01
%V 35
%N 8
%P 1621-1633
%K 
%R https://doi.org/10.1071/CH9821621
%U https://www.publish.csiro.au/paper/CH9821621 
%X The rate and regiochemistry of the SRN1 reactions of aci-nitronates with p-nitrobenzylic substrates are profoundly affected by branching at the positions adjacent to the reaction sites (C&#946;). Definitive rules which predict whether C-alkylation will occur in the association step involving p-nitrobenzylic radicals and aci-nitronate ions are formulated. &#946;-Branching causes O-alkylation or reductive processes to increase. In some cases no recognizable product formation results. Benzylic alcohols, p-nitrophenyl alkyl ketones and/or their oximes, and p-nitrophenol are among the products which result from subsequent reactions of the O-alkylation products, aci esters of benzylic alcohols. 
