Nucleophilic attack on the nitrone tautomeric form of 1-hydroxy-2- phenylindole

Article abstract of DOI:10.1016/S0040-4020(98)00205-1

1-Hydroxy-2-phenylindole exists in solution in both hydroxylamine and nitrone tautomeric forms: the latter is able to add organomelallic compounds, forming stable indolinic aminoxyls, which were also prepared for comparison by an independent way. The title compound, after irradiation with a mercury lamp lead to a spin adduct. whose identification was proved by deuteration of 1-hydroxy-2-phenylindole at different levels. A mechanism similar to that invoked in the photoreaction of phenyltert-butylnitrone with nucleophiles has been proposed in order to interpret this behaviour. A macroscale irradiation of 1-hydroxy-2-phenylindole affording several compounds has also been carried out.