Carbonyldiimidazole-mediated Lossen rearrangement.
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.
Dubé
Pascal
P
Chemical Research and Development, Pfizer Global Research and Development, Eastern Point Road, P.O. Box 8013, Groton, Connecticut 06340-8013, USA. pascal.dube@pfizer.com
Nathel
Noah F Fine
NF
Vetelino
Michael
M
Couturier
Michel
M
Aboussafy
Claude Larrivée
CL
Pichette
Simon
S
Jorgensen
Matthew L
ML
Hardink
Mark
M
D020650:Combinatorial Chemistry Techniques; D006877:Hydroxamic Acids / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D006877:Hydroxamic Acids; D007093:Imidazoles