REMOTE INTRAMOLECULAR FUNCTIONALIZATION OF ARYLNITRENIUM IONS: SYNTHESIS OF AMINO-DIHYDROPHENANTHRIDINES AND BENZOCHROMANS.

Article abstract of DOI:10.1016/S0040-4039(00)83858-7

4-Aminobenzochroman (6) and 3-amino-5-acetyl-5,6-dihydrophenanthridine (9) are synthesized by intramolecular trapping of the delocalized nitrenium ions from 3-azidobenzyl phenyl ether and 3-azido-N-benzylacetanilide, respectively.On the other hand, no cyclization product is obtained from 3-azidophenyl benzyl ether, possibly owing to an ortho-effect exerted by the oxygen atom ortho to the developing ?-aryl cation.