Amination of o-Alkenylphenols with Alkylamines via Photoinduced Proton Transfer. -The photolysis of o-alkenylphenols such as (I), (IV), and (VI) in the presence of different amines leads to the Markovnikov-type o-( aminoalkyl)phenols (III), (V), (VIII), and (IX). -(YASUDA, M.; SONE, T.; TANABE, K.; SHIMA, K.; Chem. Lett. (1994) 3, 453-456; Dep. Mater. Sci., Fac. Eng., Miyazaki Univ., Gakuen-Kibanadai, Miyazaki 889-21, Japan; EN)
Irradiation of o-alkenylphenols with alkylamines resulted in Markovnikov-type amination to give o-(1-alkylaminoalkyl)phenols in relatively good yields. The photoamination was initiated by a proton transfer from 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.
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