55010-17-8Relevant articles and documents
One-pot tandem hydrophenylation and ionic hydrogenation of 3-phenylpropynoic acid derivatives under superelectrophilic activation
Nilov, Denis I.,Vasilyev, Aleksander V.
, p. 5714 - 5717 (2015/09/29)
The reactions of esters and amides of 3-phenylpropynoic acid with strong Lewis acids AlX3 (X = Cl, Br) or conjugate Br?nsted-Lewis superacids HX-AlX3 (X = Cl, Br) in benzene and cyclohexane at room temperature afforded 3,3-diphenylpropanoic acid derivatives in up to 94% yield. This tandem reaction of the acetylene bond proceeded by hydrophenylation followed by ionic hydrogenation.
Reactions of arylacetylenic compounds with arenes in the presence of aluminum halides
Shchukin,Vasil'Ev,Grinenko
experimental part, p. 82 - 97 (2010/06/19)
Conjugated arylacetylenic ketones and aldehydes, propargyl-type alcohols, and arylacetylenes reacted with arenes in the presence of AlBr3 or AlCl3 as catalyst to give substituted indenes. 3-Arylpropynoic acids under analogous conditi
Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles
Rendy, Rendy,Zhang, Yun,McElrea, Aaron,Gomez, Alma,Klumpp, Douglas A.
, p. 2340 - 2347 (2007/10/03)
The chemistry of cinnamic acids and related compounds has been studied. In superacid-catalyzed reactions with arenes, two competing reaction mechanisms are proposed. Both mechanisms involve the formation of dicationic intermediates (superelectrophiles), and the reactions can lead to either chalcone-type products or indanone products. The direct observation of a dicationic species (by low-temperature 13C NMR) is reported. We provide clear evidence that protonated carboxylic acid groups (or the corresponding acyl cation) can enhance the reactivity of an adjacent electrophilic center. Triflic acid is also found to be an effective acid catalyst for the direct synthesis of some electron-deficient chalcones and heterocyclic chalcones from cinnnamic acids.
