Tuesday, 24 May 2005 - 9:05 AM
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This presentation is part of: Green Chemistry I

A Green Future for HMPA?

Peter Wipf, University of Pittsburgh, Pittsburgh, PA

Hexamethylphosphoramide (HMPA) has been used extensively in organic synthesis due to its unique properties as a dipolar aprotic solvent and its superior ability to form cation-ligand complexes. For example, HMPA coordinates approximately 300 times better to lithium ions than THF. HMPA has also been used catalytically, stoichiometrically, or in excess to control the stereochemistry of the product or to bias the reaction regio- and chemoselectivity. However, HMPA is also a highly toxic chemical with considerable potential carcinogenicity. Its use has been severely restricted, and there is continued need for more environmentally benign and biologically innocuous analogs. We have systematically tested polymer-linked variants and studied their synthetic properties in order to develop a green alternative to HMPA.

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