Organic Chemistry Portal



Improved Dimethylsulfoxonium Methylide Cyclopropanation Procedures, Including a Tandem Oxidation Variant

Richard J. Paxton, Richard J. K. Taylor*

*University of York, Department of Chemistry, Heslington, York, YO10 5DD, UK, Email:

R. J. Paxton, R. J. K. Taylor, Synlett, 2007, 633-637.

DOI: 10.1055/s-2007-967966

see article for more reactions


A new procedure for the cyclopropanation of enones and related systems employs trimethylsulfoxonium iodide and an organic base to generate dimethylsulfoxonium methylide in situ. Activated alcohols are converted directly into cyclopropyl ketones by a one-pot tandem oxidation-cyclopropanation sequence.

see article for more examples

gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

M. G. Edwards, R. J. Paxton, D. S. Pugh, A. C. Whitwood, R. J. K. Taylor, Synthesis, 2008, 3279-3288.

Key Words

Corey-Chaykowsky Reaction, cyclopropanes, cyclopropanations, tandem oxidation procedures, one-pot procedures, manganese(IV) oxide

ID: J60-Y2007-0550