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Photolabile Protection of Alcohols, Phenols, and Carboxylic Acids with 3-Hydroxy-2-Naphthalenemethanol

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journal contribution
posted on 03.10.2008, 00:00 authored by Anton Kulikov, Selvanathan Arumugam, Vladimir V. Popik
Irradiation of alcohols, phenols, and carboxylic acids “caged” with the (3-hydroxy-2-naphthalenyl)methyl group results in fast (krelease ≈ 105 s−1) release of the substrates with good quantum (Φ = 0.17−0.26) and chemical (>90%) yields. The initial byproduct of the photoreaction, 2-naphthoquinone-3-methide, reacts rapidly with water (kH2O = 144 ± 11 s−1) to produce parent 3-hydroxy-2-naphthalenemethanol. The o-quinone methide intermediate can be also trapped by other nucleophiles or converted into a photostable Diels−Alder adduct with ethyl vinyl ether.