65163-86-2Relevant academic research and scientific papers
AMINE OXIDATION. PART 14. ACID-CATLYSED DEOXYGENATION OF SOME N,N-DIMETHYLANILINE N-OXIDES AND REACTIONS OF THE RESULTANT IMINIUM-BENZENIUM DICATIONS
Smith, John R. Lindsay,Linford, Janet M.,McKeer, Linda C.,Morris, Paul M.
, p. 1099 - 1106 (2007/10/02)
The recations of N,N-dimethylaniline N-oxide and three substituted derivatives (4-CH3, 4-CH3O, and 4-NO2) in strong acids have been followed by 1H and 13C n.m.r. spetroscopy and product studies.These N-oxides can be deoxygenated in strong acids to give N,N-dimethyliminium-benzenium dications.With the 4-methoxy-substituted N-oxide the reaction, which is helped by the electron-releasing methoxy-substituent, proceeds at room temperature in trifluoroacetic acid (TFA).By contrast the N,N-dimethylaniline N-oxide with an electron-withdrawing 4-nitro-substituent is stable in TFA and requires the stronger acid fluorosulphonic acid for reaction to occur.The mechanisms of these reactions are discussed.
