New transition metal complexes of Co(II), Cu(II), Ni(II), and Fe(III) of the ligands 6,6 0 -(1E,1 0 E)-(4, 5-dimethyl-1,2-phenylene)bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(7-hydroxy-5-methoxy-2-methyl-4H-chromen-4-one) H 2 L 1 and 6,6'-(1E,1 0 E)-cyclohexane-1, 2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis-(7-hydroxy-5-methoxy-2-methyl-4H-chromen-4-one) H 2 L 2 have been prepared and characterized using physio-chemical and spectroscopic methods. The results obtained for the complexes indicated that the geometries of the metal centres are either square planar or octahedral. Cyclopropanation reactions of unactivated olefins by ethyldiazoacetate (EDA) in the presence of [L 1 Cu]ÁH 2 O, [L 2 Cu]Á2H 2 O and [L 2 *Co]Á 2H 2 O as catalysts were examined. The results showed that only [L 2 *Co]Á2H 2 O can act as a catalyst for the cyclopropanation reaction of unactivated olefins with very high selectivity (up to 99% based on EDA).