Nucleophilic displacements of N-aryl and heteroaryl groups. Part 1. Pyrylium-mediated transformation of anilines into phenols
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2601-2604
- https://doi.org/10.1039/p19830002601
Abstract
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) rearranged at 150 °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.Keywords
This publication has 0 references indexed in Scilit: