Photochemical generation and the reactivity of o-naphthoquinone methides in aqueous solutions

S Arumugam, VV Popik

Index: Arumugam, Selvanathan; Popik, Vladimir V. Journal of the American Chemical Society, 2009 , vol. 131, # 33 p. 11892 - 11899

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Citation Number: 64

Abstract

Irradiation of 3-hydroxy-2-naphthalenemethanol (3a) and 2-hydroxy-1- naphthalenemethanol (4a) results in efficient (Φ254= 0.17 and 0.20) dehydration and the formation of isomeric naphthoquinone methides, 2, 3-naphthoquinone-3-methide (1) and 1, 2-naphthoquinone-1-methide (2), respectively. In aqueous solution, naphthoquinone methides 1 and 2 undergo rapid hydration to regenerate starting materials (τH2O (1)= 7.4 ...