Journal of Organic Chemistry 2008-10-03

Photolabile protection of alcohols, phenols, and carboxylic acids with 3-hydroxy-2-naphthalenemethanol.

Anton Kulikov, Selvanathan Arumugam, Vladimir V Popik

Index: J. Org. Chem. 73(19) , 7611-5, (2008)

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Abstract

Irradiation of alcohols, phenols, and carboxylic acids "caged" with the (3-hydroxy-2-naphthalenyl)methyl group results in fast (k(release) approximately = 10(5) s(-1)) release of the substrates with good quantum (Phi = 0.17-0.26) and chemical (>90%) yields. The initial byproduct of the photoreaction, 2-naphthoquinone-3-methide, reacts rapidly with water (k(H2O) = 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.