128966-05-2Relevant academic research and scientific papers
Bromoamides as starting materials in the synthesis of α-hydroxy- and α- alkoxy derivatives
Cavicchioni
, p. 2223 - 2227 (1994)
Silver oxide promotes substitution of the bromine at position 2 of α- bromocarboxamides, with a hydroxyl or an alkoxyl group.
A direct functionalization of tertiary alkyl bromides with O-, N-, and C-nucleophiles
Vachal, Petr,Fletcher, Joan M.,Hagmann, William K.
, p. 5761 - 5765 (2008/02/09)
Silver oxide used in stoichiometric amounts promoted the direct functionalization of tert-alkyl bromides and provided the desired adducts in 39-96% isolated yield. Reaction of tert-bromides with carboxylic acids yielded esters, with alcohols and phenols yielded alkyl and aryl ethers, with amines and anilines yielded selectively mono-alkylated amines and anilines, and with a C-nucleophile yielded an all-carbon quaternary hydrocarbon. The method was applied to a sequential alkylation of a primary amine with two different alkyl bromides yielding selectively a tertiary amine with three different substituents in one-pot.
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.
