Journal of Organic Chemistry 2007-11-23

2,5-dihydroxybenzyl and (1,4-dihydroxy-2-naphthyl)methyl, novel reductively armed photocages for the hydroxyl moiety.

Alexey P Kostikov, Vladimir V Popik

Index: J. Org. Chem. 72(24) , 9190-4, (2007)

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Abstract

Irradiation of alcohols, phenols, and carboxylic acids "caged" with the 2,5-dihydroxybenzyl group or its naphthalene analogue results in the efficient release of the substrate. The initial byproduct of the photoreaction, 4-hydroxyquinone-2-methide, undergoes rapid tautomerization into methyl p-quinone. The UV spectrum of the latter is different from that of the caging chromophore, thus permitting selective irradiation of the starting material in the presence of photochemical products. These photoremovable protecting groups can be armed in situ by the reduction of photochemically inert p-quinone precursors.