A Different Behaviour of the Phthalimide Ion in Srn1 Reactions

Manuel Bajo Maquieira,Roberto A Rossi,Alicia B Peñéñory

doi:10.3390/50300457

Manuel Bajo Maquieira, Roberto A Rossi + Show 1 more

Open Access

https://doi.org/10.3390/50300457

Copy DOI

Abstract

The phthalimide anion reacts by the SRN1 mechanism under photostimulation with different substrates. Whilst with 1-iodonaphthalene only reduction of the naphthyl radical is observed, with 1-iodoadamantane coupling at the carbon instead of at the nitrogen takes place.

Highlights

The mechanism of Radical Nucleophilic Substitution (SRN1) is a chain process with radicals and radical anions as intermediates [1]
It is known that within the nitrogen-centered nucleophiles, aromatic amines react with aryl halides to yield the substitution product on the carbon atom and none on the nitrogen atom
The photoinduced reaction of anion 1 with 1-iodonaphthalene (3) in dimethylsulfoxide (DMSO) and in the presence of 18-crown-ether renders 72% of iodide ions after three hours and naphthalene is the only product observed

Summary

Introduction

The mechanism of Radical Nucleophilic Substitution (SRN1) is a chain process with radicals and radical anions as intermediates [1]. Different substrates and nucleophiles participate in these reactions. It is known that within the nitrogen-centered nucleophiles, aromatic amines react with aryl halides to yield the substitution product on the carbon atom and none on the nitrogen atom.

Results

Conclusion