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Pure Appl. Chem., 2004, Vol. 76, No. 3, pp. 645-649

Substrate scope in the olefin cyclopropanation reaction catalyzed by m-oxo-bis[(salen)iron(III)] complexes

S. K. Edulji and S. T. Nguyen

Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-3113, USA

Abstract: The cyclopropanation of various alkenes with different diazoester compounds was investigated using two different μ-oxo-bis[(salen)iron(III)] complexes, [Fe(3,3',5,5'-tBu4salen)]2O and [Fe(salen)]2O. Ethyl diazoacetate (EDA), tert-butyl diazoacetate (tBDA), and ethyl diazoacetoacetate (EDAA) were used with mono- and disubstituted terminal olefins (styrene and 1,1-diphenyl ethylene, respectively), internal olefin (trans-β-methyl styrene), and an electron-rich alkene (n-butyl vinyl ether). Moderate-to-good cyclopropanation yields were obtained for most substrates.