Hg_(II)-ACTIVATION IN THE CHEMOSELECTIVE SUBSTITUTION OF CHLORINE BY THE AZIDE ION IN CHLOROPHOSPHOROTHIONATE ESTERS

Abstract

In chlorophosphorothionate or dichlorophosphorothionate esters, Hg_(II)-coordination to the S-atom facilitates nucleophilic attack at P of the azide ion, to afford the corresponding azido derivatives in good yields. The chemoselectivity of this reaction vs C-substitution is also greatly improved.

Key Words:

• Azidothiophosphates
• fenthion
• Hg_(II)-catalysis
• Hg_(II)-sulphur affinity
• nucleophilic P-attack
• photoaffinity labelling