Carbonyldiimidazole-mediated Lossen rearrangement

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

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.

MeSH terms

  • Combinatorial Chemistry Techniques
  • Hydroxamic Acids / chemistry
  • Imidazoles / chemistry*
  • Models, Molecular
  • Molecular Structure

Substances

  • Hydroxamic Acids
  • Imidazoles