Regioselectivity in the Catalytic Hydrogenolysis of 1-Amino-1-cyclopropanecarboxylic Acid and Its Methyl Ester

Article abstract of DOI:10.1246/bcsj.59.2839

The title compounds were hydrogenolyzed over Pd-C.The ring-bond cleavage in the hydrogenolysis of the acid in water or methanol occurred at both the C1-C2 bond and the C2-C3 bond in nearly equal proportion, whereas the C1-C2 bond was cleaved mainly in the presence of ammonia and the C2-C3 bond was cleaved mainly in acetic acid.Selective hydrogenolysis of the C1-C2 bond of ester occurred in hexane or methanol, whereas the C2-C3 bond was hydrogenolyzed mainly in acetic acid.The role of the amino group is discussed.