Nucleophilic displacements of N-aryl and heteroaryl groups. Part 6. The rearrangement of 1-aryl-5,6,7,8-tetrahydro-8-oximino-2,6-diphenylquinolinium cations

Abstract

1 -Aryl-2-(benzyl- and neopentyl-carbamoyl) pyridinium salts (7) are rearranged by NaH at 110 °C into the corresponding 2-(N-aryl-N-substituted carbamoyl) pyridines (19). The 1 -aryl-5,6,7,8-tetrahydro-8-oximinoquinolinium salts (14) similarly give 8-(arylhydroxyamino)-5,6-dihydroquinolines (17), preferring a five- to a six-membered transition state.