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1999•Journal of the Chemical Society Perkin Transactions 2Requires access

Aromatic radical anions as possible intermediates in the nucleophilic aromatic substitution (SNAr): an EPR study

Loris Grossi, Samantha Strazzari

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Abstract

The reactions among halonitrobenzenes or polynitrobenzenes and alkoxides, thiolates or tertiary amines have provided the evidence that in a SNAr reaction type a single electron transfer from the nucleophile to the aromatic substrate, to generate two radical species within the solvent cage, can take place to some extent. The detection of radical intermediates by EPR spectroscopy, in several SNAr reactions, is reported.

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What this paper is about

The reactions among halonitrobenzenes or polynitrobenzenes and alkoxides, thiolates or tertiary amines have provided the evidence that in a SNAr reaction type a single electron transfer from the nucleophile to the aromatic substrate, to generate two radical species within the solvent cage, can take place to some extent. The detection of radical intermediates by EPR spectroscopy, in several SNAr reactions, is reported.

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Available abstract

The reactions among halonitrobenzenes or polynitrobenzenes and alkoxides, thiolates or tertiary amines have provided the evidence that in a SNAr reaction type a single electron transfer from the nucleophile to the aromatic substrate, to generate two radical species within the solvent cage, can take place to some extent. The detection of radical intermediates by EPR spectroscopy, in several SNAr reactions, is reported.

Key concepts: Nucleophilic aromatic substitution, Chemistry, Radical-nucleophilic aromatic substitution, Nucleophile, Electron paramagnetic resonance, Nucleophilic substitution, Solvent, Electrophilic aromatic substitution

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