ORGN Ahmed Abdel-Magid, Scott Sieburth  Wednesday, March 24, 2010 

1021 - Monitoring lithium dialkylcuprate conjugate additions with in situ IR spectroscopy

Jeffrey K Bratz, bratzjk@lafayette.edu, Jennifer L Rutherford. Department of Chemistry, Lafayette College, Easton, Pennsylvania 18042, United States

Lithium dialkylcuprates can undergo 1,4- (conjugate) addition with a ,b -unsaturated carbonyl compounds. In this study, we are using in situ IR spectroscopy to monitor both the formation of lithium dialkylcuprates from alkyllithiums and a copper source, and the subsequent reaction with a, b -unsaturated ketones. Variables such as the time and temperature of the cuprate formation, reaction temperature, relative equivalents of Cu:Li, and overall equivalents of cuprate have been studied. We aim to achieve a better understanding of the ideal reaction conditions for conducting a lithium dialkylcuprate-mediated conjugate addition, as well as a better mechanistic understanding of the overall reaction. Our results from following the formation of the 1,4-adduct over the course of the reaction with in situ IR spectroscopy and the relative amounts of 1,4-adduct to 1,2-adduct under the different reaction conditions will be reported.


Wednesday, March 24, 2010 07:00 PM
Chemistry for a Sustainable World, Metal-Mediated Reactions & Syntheses, Peptides, Proteins & Amino Acids, New Reactions and Methodology (07:00 PM - 09:00 PM)
Location: The Moscone Center
Room: Hall A

 

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