First single electron transfer reaction on propargylic chloride in 5-nitroimidazole series

We report here the first example of an S_RN1 reaction on propargylic chloride in heterocyclic series. The reaction of 4-(3-chloroprop-1-ynyl)-1,2-dimethyl-5-nitro-1H-imidazole with nitronate anions led to both the formation of the C-alkylated product through an S_RN1 mechanism and the predominant ethylenic compound resulting from nitrous acid elimination on the C-alkylated product. Interestingly, in contrast to our previous works on S_RN1 reactivity, no O-alkylated product was observed.