AMINATION OF O-ALKENYLPHENOLS WITH ALKYLAMINES VIA PHOTOINDUCED PROTON-TRANSFER

Irradiation of o-alkenylphenols with alkylamines resulted in Markovnik ov-type amination to give o-(1-alkylaminoalkyl)phenols in relatively g ood yields. The photo-amination was initiated by a proton transfer fro m the ammonium ion to the alkenyl group of o-alkenylphenolate anion in the excited state in the ion pair formed between the phenols and the amines. The resulting zwitter ion allowed the nucleophilic addition of the amine at the benzylic cation center.