Dedicated to Prof. H. Mayr on the occasion of his 70th birthday
Abstract
This short review provides an overview on the interaction between 1,3,5-triaminobenzene
derivatives and different kinds of electrophiles. Due to the ambident reactivity of
these nucleophiles (i.e., at the nitrogen atom of the substituents and at the aromatic
carbon atom) different compounds can be obtained. Particular attention is devoted
to the detection, isolation, and characterization of covalent intermediates of aromatic
substitution, starting from Wheland intermediates until the first detection and characterization
of Wheland–Meisenheimer intermediates.
1 Introduction
2 Reactions between 1,3,5-Triaminobenzene Derivatives and Charged Electrophiles
2.1 The Proton as an Electrophile
2.2 Arenediazonium Salts as Electrophiles
3 Reactions between 1,3,5-Triaminobenzene Derivatives and Neutral Electrophiles
3.1 Alkyl Halides as Electrophiles
3.2 Acyl Halides and Sulfonyl Chlorides as Electrophiles
3.3 Aryl Halides and Heteroaryl Halides as Electrophiles
3.4 Polynitroheteroaromatics as Electrophiles
4 Conclusion
Key words
reaction intermediates - aromatic substitution - triaminobenzenes - electrophiles
- nucleophiles - Wheland complexes - Wheland–Meisenheimer intermediates
