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The Lossen rearrangement from free hydroxamic acids

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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.

Graphical abstract: The Lossen rearrangement from free hydroxamic acids

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Publication details

The article was received on 05 Apr 2019, accepted on 08 May 2019 and first published on 08 May 2019


Article type: Review Article
DOI: 10.1039/C9OB00789J
Org. Biomol. Chem., 2019, Advance Article

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    The Lossen rearrangement from free hydroxamic acids

    M. Thomas, J. Alsarraf, N. Araji, I. Tranoy-Opalinski, B. Renoux and S. Papot, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00789J

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