Further Information
Literature
Related Reactions
Synthesis of cyclopropanes
Simmons-Smith Reaction
This reaction affords the cyclopropanation of olefins.
Mechanism of the Simmons-Smith Reaction
Ultrasonication improves the rate of formation of these organozinc compounds, as with many organometallic reactions occurring at a surface.
The mechanism has not been fully clarified, but pure carbenes can be excluded, and a metal carbenoid is likely to be involved. The following results may be interpreted to indicate a possible complexation of the active species by hydroxy groups leading to reaction on the same face as this substituent. This would only be possible if an organozinc reagent is present.
Recent Literature
Highly Enantio- and Diastereoselective Tandem Generation of Cyclopropyl
Alcohols with up to Four Contiguous Stereocenters
H. Y. Kim, A. E. Lurain, P. Garcia-Carcia, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc., 2005, 127, 13138-13139.
