
TY  - JOUR
A1  - Newcombe, PJ 
A1  - Norris, RK 
T1  - Substitution reactions of nitrothiophens. IV. Limitations in scope of the SN(AEAE) reaction in thienylalkyl derivatives
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1981
VL  - 34
IS  - 9
SP  - 1879
EP  - 1886
KW  - 
UR  - https://doi.org/10.1071/CH9811879 
N2  - 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. 
ER  -

