Carbonyldiimidazole-Mediated Lossen Rearrangement
Pascal Dubé*, Noah F. Fine Nathel, Michael Vetelino, Michel Couturier, Claude Larrive Aboussafy, Simon Pichette, Matthew L. Jorgensen and Mark Hardink
*Chemical Research and Development, Pfizer Global Research
and Development, Eastern Point Road, P.O. Box 8013, Groton, Connecticut
06340-8013, Email: pascal.dube
pfizer.com
P. Dubé, N. F. F. Nathel, M. Vetelino, M. Couturier, C. L. Abossafy, S. Pichette, M. L. Jorgensen, M. Hardink, Org. Lett., 2009, 11, 5622-5625.
DOI: 10.1021/ol9023387
Abstract
Carbonyldiimidazole mediates the Lossen rearrangement of various hydroxamic acids to isocyanates. This process is experimentally simple and mild, with imidazole and CO2 being the sole stoichiometric byproduct. The method avoids the use of hazardous reagents and thus represents a green alternative to standard processing conditions for the Curtius and Hofmann rearrangements.
see article for more examples
proposed reaction pathway
Key Words
Lossen Rearrangement, Urea Derivatives, Carbamates, Hydroxamic Acids
ID: J54-Y2009-3660
