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. 2009 Dec 17;11(24):5622-5.
doi: 10.1021/ol9023387.

Carbonyldiimidazole-mediated Lossen rearrangement

Pascal Dubé  1 , Noah F Fine Nathel, Michael Vetelino, Michel Couturier, Claude Larrivée Aboussafy, Simon Pichette, Matthew L Jorgensen, Mark Hardink
Affiliations

Carbonyldiimidazole-mediated Lossen rearrangement

Pascal Dubé et al. Org Lett. .

Abstract

Carbonyldiimidazole (CDI) was found to mediate the Lossen rearrangement of various hydroxamic acids to isocyanates. This process is experimentally simple and mild, with imidazole and CO(2) being the sole stoichiometric byproduct. Significant for large-scale application, the method avoids the use of hazardous reagents and thus represents a green alternative to standard processing conditions for the Curtius and Hofmann rearrangements.

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