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Pure Appl. Chem. 76(3), 645-649, 2004

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-b-methyl styrene), and an electron-rich alkene (n-butyl vinyl ether). Moderate-to-good cyclopropanation yields were obtained for most substrates.

*Plenary and invited lectures presented at the 12th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-12), Toronto, Ontario, Canada, 6-10 July 2003. Other lectures are published in this issue, pp. 453-695.

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