Lossen rearrangement

What is Lossen rearrangement?

The Lossen rearrangement is a chemical reaction that involves the conversion of a hydroxamic acid into an isocyanate, which can be achieved through the use of its O-acyl, sulfonyl, or phosphoryl derivative. In the presence of amines, ureas are formed. Furthermore, when water is present, amines containing one less carbon than the starting material can be obtained.

Lossen rearrangement
Lossen rearrangement

References

Lossen, W. (1872), Ueber Benzoylderivate des Hydroxylamins. [On benzoyl derivatives of hydroxylamine.] Justus Liebigs Ann. Chem., 161: 347-362. https://doi.org/10.1002/jlac.18721610219

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