Photo-Arbuzov rearrangements of cyclic phosphite systems

Abstract

The direct UV irradiation of cyclic phosphites 1– 4 was carried out in argon-saturated solvents. In all cases examined, the rearranged, ring-contracted Photo-Arbuzov phosphonate was the major product formed with isolated yields ranging from 40 to 50%. These phosphonate photoproducts, 5– 8, represent novel, bicyclic, aromatic phosphonate systems never before described in the literature of heterocyclic phosphorus chemistry. These compounds are of interest based on their potential application as ring-constrained, non-hydrolyzable mimics of phosphorylated tyrosine.