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The Lossen reaction14,15 is the rearrangement of hydroxamic acids, which are prepared from acids, acyl chlorides and esters. It is usually conducted under. Lossen Rearrangement Reaction of Aromatic and Aliphatic. Hydroxamates. By. Mirvat Sanaallah. A thesis submitted to the Faculty of Graduate Studies and. In the Lossen rearrangement, O-acylation of hydroxamic acids is a necessary step before the rearrangement, and this preliminary process.

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The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. One feature of this novel transformation is that the formamide rearrangejent triple roles in the olssen by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products.

Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives.

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The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions.


Not only monosubstituted formamides were synthesized from hydroxamic acids, but also NN -disubstituted formamides were obtained when secondary amines were used as precursors.

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Carbonyldiimidazole-Mediated Lossen Rearrangement

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