98583-83-6Relevant academic research and scientific papers
Electrochemical Reduction of 2-Bromo-carboxamides. Self-protonation Mechanism and Reaction with Dimethylformamide
Maran, Flavio,Vianello, Elio,Cavicchioni, Giorgio,D'Angeli, Ferruccio
, p. 660 (1985)
Electrochemical reduction of 2-bromo-carboxamides involves self-protonation of the electrogenerated bases and affords, among other products, cyclo-adducts incorporating a dimethylformamide unit.
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.
Electrochemistry of 2-Bromo-2-methylpropanamides. Reduction Mechanism and Cyclocoupling Reaction with Amide Solvents
Maran, Flavio,Vianello, Elio,D'Angeli, Ferruccio,Cavicchioni, Giorgio,Vecchiati, Giorgio
, p. 33 - 39 (2007/10/02)
The electrochemical reduction of series of secondary and tertiary α-bromoisobutyramides has been studied in dipolar aprotic solvents.A carbanion is formed at the mercury electrode as a consequence of two-electron C-Br bond cleavage.Voltammetry and macroelectrolysis point to a self-protonation mechanism, the carbanion undergoing protonation by a parent molecule to yield the isobutyramide.Concurrently, tertiary 2-bromoamides undergo 1,2-elimination to yield an αβ-unsaturated amide, while secondary 2-bromoamides are deprotonated at the nitrogen atom, affording a bromo-containing anion.The decay of the latter is strongly dependent on the solvent and the substituent at nitrogen.In acetonitrile, elimination and fragmentation products are identified in the electrolysed solution.On the other hand, in N,N-dimethylformamide or N,N-dimethylacetamide, the bromo-containing anion is eventually cyclocondensed onto the carbonyl group of the amide solvent, to yield an oxazolidin-4-one derivative.Preliminary data suggest that an analogous cyclocoupling reaction takes place when the reduction is carried out in 1-methyl-2-pyrrolidone.
