41412-79-7Relevant academic research and scientific papers
Original TDAE strategy using propargylic chloride: Rapid access to 1,4-diarylbut-3-ynol derivatives
Roche, Manon,Terme, Thierry,Vanelle, Patrice
, p. 1540 - 1548 (2013/04/10)
We report herein the first synthesis of propargylic alcohols using an organic reducing agent. Diarylbutynol derivatives are formed in moderate to good yields under mild conditions from the reaction of 1-(3-chloroprop-1-ynyl)-4- nitrobenzene with various aromatic aldehydes using tetrakis(dimethylamino) ethylene (TDAE) as reductant.
First Long-Distance SRN1 on a propargylic chloride
Roche, Manon,Terme, Thierry,Vanelle, Patrice
scheme or table, p. 4184 - 4187 (2012/08/29)
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-S RN1 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.
