Inter and Intramolecular Nucleophilic Substitutions of Activated Phenylselanyl Groups

Abstract

This review assembles the results of studies out in my laboratory and related to nucleophilic substitutions and cyclization reactions involving unsaturated and functionalized phenylsele-nides. Three modes of activation of the phenylselanyl group were used. The halogen treatment has produced dihalo adducts whose decomposition has led to various halogenated unsaturated and functionalized structures, sometimes with rearrangement. The PhSe⁺ activation was involved during the selenium-induced cyclization of homoallylic amines, allowing the formation of β-halopyrrolidines. The synthesis of aziridines was achieved, for the first time, through the intermediate formation of β-amino methylselenoniurn salts. Br⁺ and PhSe⁺ activations have also allowed the preparation of these azahetorocycles.

Key Words:

• Selenonium salt
• nucleophilic substitution
• dihaloselenurane
• maheterocycle
• carbonyl compound
• ester
• allylic compound