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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