Reaction pathways for ambident aryloxide O??and C??nucleophiles in SNAr displacement versus Meisenheimer complex formation with picryl halides. Stereoelectronic …

RA Manderville, JM Dust…

Index: Manderville, Richard A.; Dust, Julian M.; Buncel, Erwin Journal of Physical Organic Chemistry, 1996 , vol. 9, # 8 p. 515 - 528

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Citation Number: 12

Abstract

Abstract To probe regioselectivity in Meisenheimer complexation, the reaction of two picryl halides (PiX where X= F, Cl) with a series of aryloxide nucleophiles (phenoxide, 2, 4, 6- trimethylphenoxide and 2, 6-di-t-butylphenoxide) were monitored by 1 H NMR spectroscopy in dimethyl sulphoxide at ambient temperature and in acetonitrile-dimethoxyethane (MeCN- DME) at low temperature (− 40 C). The reactions of both picryl halides with the ambident ( ...