A study of the condenstaion of arenediols with phenylphosphonic dichloride: The process of ring opening in certain bicyclic phosphonates leading to substituted O-hydroxyaryl hydrogen phenylphosphonates

Abstract

Phenylphosphonic dichloride condenses with 4-chlorocatechol, 3,4-dihydroxypropiophenone, and 2,3-naphthalenediol to give strong acids via hdyrolytic ring-cleavage involving the corresponding intermediate bicyclic phosphonates. Proof of structure for the two acids in the catechol series consisted of degradation to derivatives of guaiacol. A nucleophilic attack by water on phosphorus is postulated as the initial step in the hydrolysis.