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Toward a Stable Hydroxyphosphorane

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journal contribution
posted on 21.12.2001, 00:00 by Robert E. Hanes, Vincent M. Lynch, Eric V. Anslyn, Kevin N. Dalby
Hydroxy-pentaoxy-phosphoranes are transient intermediates formed during the hydrolysis of various phosphoesters. Kinetic analyses support the existence of such compounds, although they are not isolated. In an attempt to create a stable example, 2 equiv of a ligand possessing a very high effective molarity were attached to a central phosphorus. Instead of obtaining a hydroxyphosphorane, analysis by 31P and 19F NMR spectroscopy and X-ray crystallography showed the product to be a phosphotriester. The reason for this is discussed.