89409-10-9Relevant academic research and scientific papers
Nucleophilic Displacements of N-Aryl and Heteroaryl Groups. Part 1. Pyrylium-mediated Transformation of Anilines into Phenols
Katritzky, Alan R.,Langthorne, Ronald T.,Muathin, Hussni A.,Patel, Ranjian C.
, p. 2601 - 2604 (2007/10/02)
Aromatic amines with 2,4-diphenyl-5,6,7,8-tetrahydrochromenylium trifluoromethanesulphonate (5) gave the corresponding pyridinium salts (6; R = aryl) which were converted by base into the anhydrobases (7).Benzoyl chloride converted (7) into the new pyridinium anhydrobases (9).These anhydrobases (9) rearrangement at 150 deg C into the isomeric phenol enol ethers (10) which were readily hydrolysed to yield the corresponding phenols.The mechanistic and synthetic significance of the results are assessed.
