Lossen Rearrangement

 

Definition:

Conversion of a hydroxamic acid derivatives to an isocyanate via the intermediacy of its O-acyl, sulfonyl, or phosphoryl derivative.

                       

 

Frequency of appearance:

        This bar graph represents all of the online articles that were found to contain this specific name reaction in the title of the article. Tetrahedron letters, Tetrahedron, Synthetic letters, Synthesis, Journal of Organic Chemistry and Journal of the American Chemical Society are represented here. This table by no means represents the periodicity of the name reaction found in the literature.

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Original references:

  1. W. Lossen, Ann. 161, 347 (1872); 175, 271, 313 (1874).

 

Recent academic references:   Click here for more references

 

  1. A Novel, General Method for the Synthesis of Nitrile Oxides: Dehydration of O-Silylated Hydroxamic Acids
  • Muri, D.; Bode, J. W.; Carreira, E. M.; Org. Lett.; 2000; 2(4); 539-541.

 

  1. Degradative Rearrangements of N-(t-Butyloxycarbonyl)-O-methanesulfonyl-hydroxamic Acids: A Novel, Reagent-Based Alternative to the Lossen Rearrangement1
  • Stafford, J. A.; et al., J. Org. Chem.; 1998; 63(26); 10040-10044.  

 

  1. Spontaneous Lossen Rearrangement of (Phosphonoformyl)hydroxamates. The Migratory Aptitude of the Phosphonyl Group
  • Salomon, C. J.; Breuer, E.; J. Org. Chem.; 1997; 62(12); 3858-3861.  

                       

 

Recent process references:

 

 

Mechanism: http://www.arkat.org/arkat/journal/Named Reactions/Lossen.htm

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Scope and Limitations:

 

Synonyms:

 

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