38352-81-7Relevant academic research and scientific papers
Base-induced cyclization of derivatives of bispropargylated acetic acid to m -toluic acid
Ali, Tammar Hussein,Heidelberg, Thorsten,Hussen, Rusnah Syahila Duali
supporting information, p. 1361 - 1364 (2015/06/16)
A base-induced cyclization reaction of 1,1-bispropargyls has been examined. Alkali treatment of 2,2-bispropynyl acetic acid derivatives in aqueous ethanol mostly provided 3-methylbenzoic acid. Investigations on substituent effects indicate the requirement of an electron-withdrawing group causing CH acidity and the center of the dipropargylic structure. Besides, an intramolecular hydrogen transfer causing the rearrangement of one terminal alkyne into a corresponding allene appears to be essential. Despite an unsatisfying conversion yield of below 40%, the reaction is interesting due to the mild cyclization conditions.
Gold-catalyzed 1,3-acyloxy migration/5-exo-dig cyclization/1,5-acyl migration of diynyl esters
Lebuf, David,Simonneau, Antoine,Aubert, Corinne,Malacria, Max,Gandon, Vincent,Fensterbank, Louis
supporting information; experimental part, p. 6868 - 6871 (2011/08/06)
Working three shifts: Polyconjugated δ-diketones are formed stereoselectively in high yields by the gold-catalyzed rearrangement of 1,6-diyn-3-yl esters. This cascade involves a 1,3-sigmatropic acyloxy shift, a 5-exo-dig cyclization of the resulting allenyne, and an unprecedented 1,5-sigmatropic shift of an acyl fragment. The usefulness of the products was shown by an efficient acid-catalyzed transformation into a complex polycyclic framework. Copyright
