Synthesis and reactivity of small phosphorus-containing dendritic wedges(dendrons)

Abstract

The synthesis of two small dendrons (dendritic wedges) is reported and the reactivity of the functionality located at the core is studied. The first dendron has no reactive functionality on the surface, but possesses a vinyl group activated by a P=N-P=S linkage at the core; this vinyl group reacts slowly but cleanly with 2,3-dimethylbutadiene in Diels-Alder additions. The second dendron has aldehyde groups on the surface and one protected phenol group at the core. The deprotection occurs in very mild conditions, leading to a dendron having one phenol and four aldehyde groups. The reactivity of the phenol is demonstrated by the addition of a diisocyanate, affording a carbamate function and the grafting of an isocyanate group at the core of the dendron.