110228-40-5Relevant articles and documents
Favorskii-like rearrangement of an aliphatic α-halo amide
Kelly, Nicholas M.,Wellejus, Anja,Elbrond-Bek, Heidi,Weidner, Morten Sloth,Jorgensen, Signe Humle
, p. 1243 - 1249 (2013)
The reaction of the α-bromoamide 2a with 1-cyclopentylpiperazine gives the Favorskii-like rearranged product 4 when the reaction is heated to 70 °C in a mixture of aqueous potassium hydroxide and ethanol. However, when solid sodium carbonate/potassium iodide is used in ethanol, the nonrearranged product 3a is formed instead. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
The Conversion of Phenols to Primary and Secondary Aromatic Amines via a Smiles Rearrangement
Coutts, Ian G. C.,Southcott, Mark R.
, p. 767 - 771 (2007/10/02)
The conversion of phenols to 2-aryloxy-2-methylpropanamides (1) and the Smiles rearrangement of these to N-aryl-2-hydroxy-2-methyl propanamides are described; hydrolysis of the latter compounds yields anilines.The scope and limitations of reaction are discussed.Routes, some involving α-lactams, from phenols to N-substituted derivatives of (1) have been developed.Under the conditions of the Smiles rearrangement these secondary 2-methylpropanamides can form directly anilides, N-alkylanilines, or benzoxazinones.