22101-03-7Relevant academic research and scientific papers
Friedel-Crafts alkylation of benzene with α,β-unsaturated amides
Koltunov, Konstantin Yu.,Walspurger, Stéphane,Sommer, Jean
, p. 3547 - 3549 (2004)
A variety of α,β-unsaturated amides (RHC=CH 2CONR′2, R=H, Me, Ar; R′=H or Et) readily condense with benzene at room temperature in the presence of an excess of aluminum chloride to give the corresponding 3-phenylpropionamides in excellent yields. This simple, one-pot procedure proved to be efficient and very clean. The mechanism of these and related reactions is discussed and the participation of superelectrophilic dicationic intermediates is suggested.
The acid-mediated ring opening reactions of α-aryl-lactams
King, Frank D.,Caddick, Stephen
supporting information; experimental part, p. 3244 - 3252 (2012/06/01)
4-Aryl-azetidin-2-ones (β-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl ex
Superacidic activation of α,β-unsaturated amides and their electrophilic reactions
Koltunov, Konstantin Yu.,Walspurger, Stephane,Sommer, Jean
, p. 4039 - 4047 (2007/10/03)
The electrophilic reactivity of α,β-unsaturated amides towards weak nucleophiles such as arenes and cyclohexane, initiated either with triflic acid (CF3SO3H) or with excess AlCl3, has been studied. The amides generally condense readily with aromatics in the presence of AlCl3 to give 3-arylpropionamides and related compounds in excellent yields, while some amides also undergo selective ionic hydrogenation with cyclohexane to give saturated amides. The proposed mechanism of these reactions involves dicationic intermediates (superelectrophiles). The direct observation of a dicationic species (by low-temperature NMR) is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
