Mild and Rapid Method for the Generation of ortho-(Naphtho) quinone Methide Intermediates

A Shaikh, AJA Cobb, G Varvounis

Index: Shaikh, Abdul Kadar; Cobb, Alexander J. A.; Varvounis, George Organic Letters, 2012 , vol. 14, # 2 p. 584 - 587

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Citation Number: 21

Abstract

A new mild method has been devised for generating o-(naphtho) quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl (or 1-naphthylmethyl) nitrate. The reactive o-(naphtho) quinone methide intermediates were trapped by C, O, N, and S nucleophiles and underwent “inverse electron-demand” hetero-Diels–Alder reaction with dienophiles to give stable adducts. The method has useful potential application in ...