Competitive Formation of β-Amino Acids,Propenoic, and Ylidenemalonic Acids by the Rodionov Reaction from Malonic Acid,Aldehydes, and Ammonium Acetate in Alcoholic Medium

The Rodionov reaction of 49 available aliphatic and aromatic aldehydes with malonic acid and ammonium acetate in alcoholic medium, resulting in formation of β-amino acids, propenoic, and ylidenemalonic acids, was studied. Certain regioselectivity regularities of the reaction were revealed. Among the variety of ketones studied, cyclohexanone is the only whose reaction yields a β-amino acid. Unusual dehydrofluorination of 6-chloro-2-fluorocinnamic acid under the Rodionov reaction was discovered.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 7, 2005, pp. 1177–1186.Original Russian Text Copyright © 2005 by Lebedev, Lebedeva, Sheludyakov, Kovaleva, Ustinova, Kozhevnikov.