Nucleophilic Displacements of N-Aryl and Heteroaryl Groups. Part 1. Pyrylium-mediated Transformation of Anilines into Phenols

DOI: 10.1039/P19830002601

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2601 - 2604 (1983)

Update date:2022-08-03

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Authors:

Katritzky, Alan R.

Langthorne, Ronald T.

Muathin, Hussni A.

Patel, Ranjian C.

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Article abstract of DOI:10.1039/P19830002601

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.

Full text of DOI:10.1039/P19830002601

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