Dual reactivity of hydroxy-and methoxy-substituted o-quinone methides in aqueous solutions: hydration versus tautomerization.

S Arumugam, VV Popik

Index: Arumugam, Selvanathan; Popik, Vladimir V. Journal of Organic Chemistry, 2010 , vol. 75, # 21 p. 7338 - 7346

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Citation Number: 16

Abstract

4-Hydroxy-6-methylene-2, 4-cyclohexadien-1-one (1) and 4-methoxy-6-methylene-2, 4- cyclohexadien-1-one (2) were generated by efficient (Φ= 0.3) photodehydration of 2- (hydroxymethyl) benzene-1, 4-diol (3a) and 2-(hydroxymethyl)-4-methoxyphenol (4a), respectively. o-Quinone methides 1 and 2 can be quantitatively trapped as Diels− Alder adducts with ethyl vinyl ether or intercepted by good nucleophiles, such as azide ion (k N3 ...