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Title:Chiral Homoenolate Synthetic Equivalents: Mechanistic, Structural, and Kinetic Investigations
Author(s):Pippel, Daniel James
Doctoral Committee Chair(s):Beak, Peter
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:The lithiation of N-Boc-N-( p-methoxyphenyl)-3-cyclohexylallylamine by n-BuLi/(-)-sparteine was examined kinetically by means of in situ infrared spectroscopy. The reaction is first order in allylic amine and zero-order in 1:1 base/ligand complex. When the relative concentrations of n-BuLi and (-)-sparteine are not held constant, the reaction exhibits an inverse dependence on n-BuLi concentration. The experimental results are rationalized by a generalized mechanism that is consistent with thermodynamic parameters, an extremely high isotope effect, and computer simulations.
Issue Date:2000
Type:Text
Language:English
Description:237 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2000.
URI:http://hdl.handle.net/2142/84493
Other Identifier(s):(MiAaPQ)AAI9990108
Date Available in IDEALS:2015-09-25
Date Deposited:2000


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