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

A Kulikov, S Arumugam, VV Popik

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

Full Text: HTML

Citation Number: 29

Abstract

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 ...

Related Articles:

Deprotection of Homoallyl (hAllyl) Derivatives of Phenols, Alcohols, Acids, and Amines

[Zhou, Yuhan; Gao, Guchao; Li, Hui; Qu, Jingping Tetrahedron Letters, 2008 , vol. 49, # 20 p. 3260 - 3263]

Highly efficient system for reduction of carboxylic acids and their derivatives to alcohols by HfCl4/KBH4

[Zhang, Jianghua; Gao, Xinqin; Zhang, Chengyi; Ma, Jianfei; Zhao, Defeng Synthetic Communications, 2009 , vol. 39, # 9 p. 1640 - 1654]

One-Pot Ortho Hydroxylations of 2-(1-Hydroxyalkyl) naphthalenes and (1-Hydroxyalkyl) benzenes

[Tanoue, Yasuhiro; Terada, Akira; Seto, Iwao; Umezu, Yasuo; Tsuge, Otohiko Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 1221 - 1224]

More Articles...