Efficient 1, 4 addition of 1-fluoro-bis(phenylsulfonyl)methane to alpha, beta unsaturated compounds

ORGN 146

G. K. Surya Prakash, gprakash@usc.edu, Sujith Chacko, chacko@usc.edu, Habiba Vaghoo, and George A. Olah, olah@usc.edu. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661
The 1, 4 addition of a fluoromethyl nucleophile to a variety of alpha, beta unsaturated compounds has been achieved for the first time under normal conditions. 1-Fluoro-bis(phenylsulfonyl)methane can be easily deprotonated under mild basic conditions to afford the corresponding soft nucleophile that readily undergoes Michael addition to alpha, beta unsaturated -ketones, -esters, -nitriles, -sulfones, as well as propynoates and alkynones at room temperature to yield the adducts in moderate to excellent yields.
 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

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