![9,9'-Spirobi[fluoren]-2-amine structure](https://static.chemtradehub.com/structs/118/118951-68-1-0d14.webp "9,9'-Spirobi[fluoren]-2-amine structure")
The Lossen rearrangement from free hydroxamic acids
Literature Information
Publication Date
2019-05-08
DOI
10.1039/C9OB00789J
Impact Factor
3.876
Authors
Mikaël Thomas, Jérôme Alsarraf, Nahla Araji, Isabelle Tranoy-Opalinski, Brigitte Renoux, Sébastien Papot
View Original
Abstract
The Lossen rearrangement, that allows the conversion of hydroxamic acids into isocyanates, was discovered almost 150 years ago. For more than a century, this transformation was supposed to occur exclusively in the presence of stoichiometric amounts of activating reagents devoted to promoting the dehydration of primary hydroxamic acids. Very recently, it was demonstrated that the Lossen rearrangement can take place directly from free hydroxamic acids offering a renewal of interest for such a reaction. This short review summarizes advances in this field by describing successively the metal-assisted, the self-propagative and the promoted self-propagative Lossen rearrangement with a special emphasis on their mechanisms.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
![Sodium 6-amino-3-[(E)-{4-[(E)-(4-aminophenyl)diazenyl]-2-methoxy-5-methylphenyl}diazenyl]-4-hydroxy-2-naphthalenesulfonate structure](https://static.chemtradehub.com/structs/294/2945-96-2-092f.webp "Sodium 6-amino-3-[(E)-{4-[(E)-(4-aminophenyl)diazenyl]-2-methoxy-5-methylphenyl}diazenyl]-4-hydroxy-2-naphthalenesulfonate structure")
Sodium 6-amino-3-[(E)-{4-[(E)-(4-aminophenyl)diazenyl]-2-methoxy-5-methylphenyl}diazenyl]-4-hydroxy-2-naphthalenesulfonate
CAS Number:
2945-96-2
Molecular Formula:
C24H21N6NaO5S
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