High-load, oligomeric phosphonyl dichloride: facile generation via ROM polymerization and application to scavenging amines

A new ROMP-derived scavenging reagent, oligomeric phosphonyl dichloride (OPC), with high-load and selectivity is reported. This reagent can be readily generated via the ROM polymerization of bicyclo[2.2.1]hept-5-en-2-ylphosphonic dichloride, which is conveniently assembled from the Diels-Alder reaction of cyclopentadiene and vinyl phosphonic dichloride. The OPC has been exploited in the rapid, efficient scavenging of primary and secondary amines that are present in excess following a common benzoylation event at room temperature (30-60 min) or under microwave conditions in shorter duration (<5 min).