Structural and rate studies of n-BuLi mediated 1,2-addition in ether-diamine mixture

ORGN 27

Bo Qu and David B. Collum. Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853
Ethers or ether-diamine mixtures are often used in organolithium reactions. In this study, we performed detailed rate studies on the 1,2-addition of n-BuLi to imines in commonly used ethers (such as THF, THP) and bidentate diamines (N,N,N',N'-tetramethylethylenediamine, TMEDA, N,N,N',N'-tetramethylcyclohexanediamine, TMCDA). Our results show that the diamine ligand does not participate in the transition state and only serves to retard the reaction.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- 201B, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004