Knorr cyclizations and distonic superelectrophiles
(Chemical Equation Presented) The acid-catalyzed Knorr cyclization has been studied by experimental and theoretical methods. The results of these studies indicate that β-ketoamides such as acetoacetanilide undergo diprotonation at the two carbonyl oxygen atoms to form distonic superelectrophiles. Direct observation of a dicationic superelectrophile was achieved by low-temperature 1H, 15N, and 13C NMR from FSO 3H-SbF5-SO2ClF solutions. In synthetic studies, the Bronsted superacid CF3SO3H is found to be an effective acid catalyst for the Knorr cyclization.
Sai, Kiran Kumar Solingapuram,Gilbert, Thomas M.,Klumpp, Douglas A.
p. 9761 - 9764
(2008/03/27)
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