title: Carbonyldiimidazole-mediated Lossen rearrangement.
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.
authors.affiliation: 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
authors.forename: Pascal
authors.initials: P
authors.lastname: Dubé
authors.forename: Noah F Fine
authors.initials: NF
authors.lastname: Nathel
authors.forename: Michael
authors.initials: M
authors.lastname: Vetelino
authors.forename: Michel
authors.initials: M
authors.lastname: Couturier
authors.forename: Claude Larrivée
authors.initials: CL
authors.lastname: Aboussafy
authors.forename: Simon
authors.initials: S
authors.lastname: Pichette
authors.forename: Matthew L
authors.initials: ML
authors.lastname: Jorgensen
authors.forename: Mark
authors.initials: M
authors.lastname: Hardink
mesh_terms: D020650:Combinatorial Chemistry Techniques; D006877:Hydroxamic Acids / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D006877:Hydroxamic Acids; D007093:Imidazoles