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Stereoselective Formation of Alkenyl Halides via Magnesium Halide Promoted Ring Opening of Bis-Activated Cyclopropenes

Yi Wang and Hon Wai Lam*

*School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, United Kingdom, Email:

Y. Wang, H. W. Lam, J. Org. Chem., 2009, 74, 1353-1355.

DOI: 10.1021/jo802475x (free Supporting Information)


Various bis-activated cyclopropenes undergo highly stereoselective ring-opening reactions to produce multisubstituted alkenyl halides in the presence of stoichiometric magnesium halides. Trapping of the magnesium enolate intermediates in situ allows the synthesis of highly functionalized compounds.

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Key Words

Cyclopropenes, Alkenyl Iodides, Alkenyl Bromides, Alkenyl Chlorides, 1,4-Additions, Multicomponent Reactions

ID: J42-Y2009-0420