80577-97-5Relevant academic research and scientific papers
Substitution Reactions of Nitrothiophens. IV Limitations in Scope of the SN(AEAE) Reaction in Thienylalkyl Derivatives
Newcombe, Peter J.,Norris, Robert K.
, p. 1879 - 1886 (2007/10/02)
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-nitrothiophen, 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 occurence of SN(AEAE) reactions with other nucleophiles is difficult to prove but benzenethiolate and 4-nitro-2-thienylmethyl acetate do react b y this mechanism to give a moderate yield of 4-nitro-2-thienylmethyl phenyl sulfide.
