Article

Author:

Segstro Edward Paul,Davie Kerry,Huang Xiaoling,Janzen Alexander Frank

Abstract

The equilibrium in the Ph2P(O)OC6H4OH-base system may be shifted by varying the base concentration, where base = imidazole, triethylamine, dimethyl sulfoxide, pyridine, and 1,4-dioxane. This equilibrium was studied by 31P and 1H NMR, and information about the symmetry of phosphorus-containing intermediates is provided by the 1H NMR spectrum of the catecholyl ring, with its ABCD spin system. The equilibrium is also affected by trifluoroacetic acid. A mechanism is proposed that involves protonation-deprotonation, cyclic-acyclic equilibria, and selective P-O bond cleavage, with all steps occurring rapidly on the NMR time scale.Key words: Ph2P(O)OC6H4OH-base system, cyclic-acyclic equilibrium, and selective P-O bond cleavage.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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