
%0 Journal Article
%A Newcombe, PJ 
%A Norris, RK 
%T Substitution reactions of nitrothiophens. IV. Limitations in scope of the SN(AEAE) reaction in thienylalkyl derivatives
%J Australian Journal of Chemistry
%D 1981/09/01
%V 34
%N 9
%P 1879-1886
%K 
%R https://doi.org/10.1071/CH9811879
%U https://www.publish.csiro.au/paper/CH9811879 
%X The reactions of 5-nitro-3-thienylethyl chloride and acetate with lithium 2-nitropropan-2-ide (1)give excellent yields of the C-alkylate, 4-(1,2-dimethyl-2-nitropropyl)-2-nitrothophen, by the SN(AEAE)mechanism. The cyano group is not a sufficiently activating substituent to support the SN(AEAE)process and 4-cyano-2-thienyl-methyl and -ethyl chlorides with the salt (1) give O-alkylated products by an SN2 mechanism. The occurrence of SN (AEAE) reactions with other nucleophiles is difficult to prove but benzenethiolate and 4-nitro-2-thienylmethyl acetate do react by this mechanism to give a moderate yield of 4-nitro-2-thienylmethyl phenyl sulfide. 
