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

A Kulikov, S Arumugam, VV Popik

文献索引：Kulikov, Anton; Arumugam, Selvanathan; Popik, Vladimir V. Journal of Organic Chemistry, 2008 , vol. 73, # 19 p. 7611 - 7615

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被引用次数: 29

摘要

Irradiation of alcohols, phenols, and carboxylic acids “caged” with the (3-hydroxy-2- naphthalenyl) methyl group results in fast (k release≈ 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 (k H2O= 144±11 s− 1) to produce parent 3-hydroxy-2-naphthalenemethanol. The o-quinone methide ...