First Long-Distance SRN1 on a propargylic chloride

We report here the first example of a Long-Distance SRN1 (LD-SRN1) reaction on a propargylic chloride. The reaction of 1-(3-chloroprop-1-ynyl)-4-nitrobenzene (1) with nitronate anions led to both the formation of the C-alkylation product through an LD-SRN1 mechanism and the ethylenic compound resulting from nitrous acid elimination on the C-alkylation product 2. In contrast with previous work on LD-SRN1 reactivity, no O-alkylation product was observed. Only one original product 4 was isolated under phase transfer conditions, resulting from a nucleophilic attack by 2-nitropropane anion on the electrophilic alkyne. This LD-SRN1 reactivity did not extend to sulfinate anions; the reaction of 1 with sulfinate anions yielded original ethylenic disulfone compounds which were formed via an ionic process.