Nucleophilic displacements of N-aryl and heteroaryl groups. Part 1. Pyrylium-mediated transformation of anilines into phenols
作者:Alan R. Katritzky、Roland T. Langthorne、Hussni A. Muathin、Ranjan C. Patel
DOI:10.1039/p19830002601
日期:——
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
与2,4
-二苯基-5,6,7,8-四
氢氧化铬三
氟甲烷磺酸酯的芳香胺(5)得到相应的
吡啶鎓盐(6; R =芳基),然后通过碱将其转化为脱
水碱(7)。
苯甲酰氯将(7)转化为新的
吡啶鎓脱
水碱(9)。这些无
水碱(9)在150℃下重排成异构的
酚烯醇醚(10),它们易于
水解得到相应的
酚。评估结果的机理和综合意义。