92929-30-1Relevant articles and documents
Studies on Tertiary Amine Oxides. LXXVII. The Pseudo-Gomberg Reaction of 4- and 2-Aminopyridine 1-Oxides
Saeki, Seitaro,Kondo, Sachiko,Hayashi, Takaaki,Hamana, Masatomo
, p. 1780 - 1789 (2007/10/02)
The 1-oxido-4-pyridyl radical generated by the reaction of 4-aminopyridine 1-oxide with amyl nitrite reacted smoothly with aromatic hydrocarbons, including five-membered heterocycles, i.e. thiophene, fyran and pyrrole, to give the arylated products when acetic acid was used as the solvent.The relative rates of reaction with the 1-oxido-4-pyridyl radical indicated that this radical is electrophilic, and this finding was supported by a comparison of molecular orbital energy levels. 2-Aminopyridine 1-oxide also undergoes a similar reaction.Keywords - pyridine N-oxide; Gomberg reaction; phenylpyridine; thienylpyridine; furylpyridine; 1-methanesulfonyl-pyrrolylpyridine; 1-oxido-4-pyridyl radical; molecular orbital; highperformance liquid chromatography