Abstract
Abstract We report here the first example of an S RN 1 reaction on propargylic chloride in heterocyclic series. The reaction of 4-(3-chloroprop-1-ynyl)-1,2-dimethyl-5-nitro-1 H -imidazole with nitronate anions led to both the formation of the C-alkylated product through an S RN 1 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 RN 1 reactivity, no O-alkylated product was observed.
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