Reductively activated "Polar" nucleophilic aromatic substitution. III. The reactions of polyfluoronitrobenzenes with methanol

Mohammed Niat, Jorge Marquet, Iluminada Gallardo, Maria Cervera, Miquel Mir

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6 Citations (Scopus)

Abstract

The nucleophilic aromatic substitution reactions of pentafluoronitrobenzene (PFNB) and 2,3,4,5-tetrafluoronitrobenzene with methanol are both reductively activated. However, the first one is sensitive to the presence of radical scavengers but the second is not. In addition, the kinetic behavior of both reactions in the absence of stimulation is very similar suggesting they are examples of second stage rate determining SNAr mechanism. Kinetic studies also show that no real photochemical stimulation exist in those reactions. The reported facts are not compatible with the previously proposed (for the reaction of PFNB with methanol) SRN2 mechanism. A new mechanistic rationale is discused. © 1994.
Original languageEnglish
Pages (from-to)9059-9062
JournalTetrahedron Letters
Volume35
Issue number48
DOIs
Publication statusPublished - 28 Nov 1994

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