Abstract
Triphenylphosphine and diisopropyl azodicarboxylate react with phenols in tetrahydrofuran or chloroform at 0° to give diaryloxytriphenylphosphoranes. A linear free-energy relationship has been found between the 31P n.m.r. chemical shifts of many of these phosphoranes and the acid dissociation constants of the corresponding phenols. In general, electron-withdrawing groups on the phenol result in downfield 31P n.m.r. chemical shifts, while electron donating groups result in up-field shifts.
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