Retro-Diels-Alder Reaction of 4 H-1, 2-Benzoxazines to Generate o-Quinone Methides: Involvement of Highly Polarized Transition States

H Sugimoto, S Nakamura…

Index: Nakamura, Satoshi; Sugimoto, Hiromichi; Ohwada, Tomohiko Journal of the American Chemical Society, 2007 , vol. 129, # 6 p. 1724 - 1732

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Citation Number: 22

Abstract

Here, we describe mechanistic studies of the retro-Diels-Alder reaction of 4 H-1, 2- benzoxazines bearing various substituents on the benzene ring. 4 H-1, 2-Benzoxazines are very simple, but quite new, heterocyclic compounds that afford substituted o-quinone methides (o-QMs) through retro-Diels-Alder reaction under mild thermal conditions. The resultant o-QMs undergo Diels-Alder reaction in situ with dienophiles to give phenol and ...