128965-68-4Relevant articles and documents
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.
