Metallo-phosphonate chemistry in ionic liquids

ORGN 619

Anh P. Vu, apvu@loyno.edu, Laura K. Byington Congiardo, lkbyingt@loyno.edu, Erika A. Shaffer, eashaffe@u.washington.edu, Robert Hartsock, hartsock@stanford.edu, W. David Stegbauer, wdstegba@loyno.edu, Aaron R. Barnum, arbaru1@lsu.edu, and D. Andrew Knight, daknight@loyno.edu. Department of Chemistry, Loyola University, 6363 St. Charles Avenue, New Orleans, LA 70118
Phosphonium salt ionic liquids can tolerate highly reactive bases such as sodium metal without decomposition. We have been studying the Michaelis-Becker (M-B) reaction in a number of ionic liquids including the phosphonium salt Cyphos IL101 and imidazolium based salts. Whilst phosphonium salts will tolerate pre-formed metallophosphonates as reagents for the M-B reaction, the use of sodium hydroxide as a base results in decomposition of the phosphonium salt to a phosphine oxide. We describe our efforts to tailor the ionic liquid to a particular base used in the M-B reaction, and NMR studies of phosphite anions formed in situ in ionic liquids.
 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008