Metal-assisted Lossen rearrangement

The Journal of Organic Chemistry
Lucie JašíkováJana Roithová

Abstract

A new reaction mechanism for the Lossen rearrangement of hydroxamic acids catalyzed by basic salts is presented. It is shown that the rearrangement proceeds in metal complexes of deprotonated hydroxamic acids. The deprotonation can occur either at the oxygen atom (observed for the zinc complexes) or at the nitrogen atom (observed for the potassium complexes). Both anionic forms are characterized by infrared multiphoton dissociation spectroscopy. The rearrangements proceed from the reactive N-deprotonated metal hydroxamates and lead to metal carbamates. The mechanism is elucidated by computational chemistry, mass-spectrometric studies, and preparative experiments.

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Citations

Apr 15, 2016·Organic Letters·Patrick S Fier, Kevin M Maloney
Jan 27, 2017·Journal of the American Chemical Society·Erik AndrisJana Roithová
Sep 3, 2013·Macromolecular Rapid Communications·Maike UnverferthMichael A R Meier
May 16, 2019·Organic & Biomolecular Chemistry·Mikaël ThomasSébastien Papot
Aug 14, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Giulio BrescianiFabio Marchetti
Nov 18, 2020·European Journal of Medicinal Chemistry·Nicola RelittiGiuseppe Campiani
Jan 25, 2014·The Journal of Organic Chemistry·Alexandra TsybizovaJana Roithová

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