Collect. Czech. Chem. Commun. 1996, 61, 1798-1804

[OsH4(PPh3)3]: New Catalyst for the Selective Cyclopropanation of Activated Olefins

Albert Demonceaua, François Simala, Corine A. Lemoinea, Alfred F. Noelsa, Igor T. Chizhevskyb and Pavel V. Sorokinb

a Laboratory of Macromolecular Chemistry and Organic Catalysis, C.E.R.M., University of Liège, Sart-Tilman (B.6a), B-4000 Liège, Belgium
b A. N. Nesmeyanov Institute of Organo-Element Compounds, Russian Academy of Sciences, 28 Vavilov Str., 117813 Moscow, Russian Federation


The title compound was found to be an efficient catalyst for the selective cyclopropanation of activated olefins by ethyl diazoacetate. The cyclopropane yields range from moderate to good (75 to 95%) for activated olefins such as styrene and styrene derivatives, but are rather low (20 to 30%) for non-activated olefins such as terminal and cyclic alkenes. In the intermolecular competition, styrene was 45 times more reactive than cyclooctene. In all cases, trans (exo) cyclopropane predominated over the cis (endo) isomer.

Keywords: Olefins; Diazo compounds; Cyclopropanation; Osmium; Catalysis.