Synthesis and applications of oligomeric sulfide and sulfonium salts derived from ROM polymerization

ORGN 194

Mianji Zhang, mizhang@ku.edu, University of Kansas, Lawrence, KS 66047, Daniel L. Flynn, dflynn@deciphera.com, Deciphera Pharmaceuticals LLC, 4950 Research Park Way, Lawrence, KS 66047, and Paul R. Hanson, phanson@ku.edu, Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, NIH Center of Excellence in Chemical Methodologies and Library Development (KU-CMLD), Lawrence, KS 66045-7582.
The development of high-load soluble oligomeric sulfide and a series of insoluble oligomeric sulfonium salts using ring-opening metathesis polymerization (ROMP) of norbornenyl-tagged monomers is reported. The oligomeric sulfonium salts are isolated as free-flowing, stable powders, and have been used for the N-, O- and S-alkylation of amines, phenols, and thiophenols, respectively. Moreover, ionic liquids [(bmim)PF6] have been shown to facilitate the alkylation event and increase the reaction rate. Overall, these approaches involve solution-phase or solid-phase reactions followed by precipitation/filtration of the reaction byproducts to afford pure products in high yields and purities.
 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005