NDLI: Lithium hexamethyldisilazide-mediated enolizations: influence of chelating ligands and hydrocarbon cosolvents on the rates and mechanisms.

Content Provider	Semantic Scholar
Author	Godenschwager, Peter F. Collum, David B.
Copyright Year	2007
Abstract	Enolizations of 2-methylcyclohexanone by lithium hexamethyldisilazide (LiHMDS) in the presence of three chelating ligands-trans-N,N,N',N'-tetramethylcyclohexanediamine, N,N,N',N'-tetramethylethylenediamine, and dimethoxyethane-reveal an approximate 40-fold range of rates. NMR spectroscopic analyses and rate studies reveal isostructural transition structures based on monomeric LiHMDS for the diamines. Rate studies of LiHMDS/dimethoxyethane-mediated enolizations implicate a substantial number of monomer- and dimer-based mechanisms. The rate laws vary for the three ligands because of ligand-dependent structural differences in both the reactants and the transition structures. The importance of LiHMDS-ketone complexes and the role of hydrocarbon cosolvents are discussed.
File Format	PDF HTM / HTML
DOI	10.1021/ja074018m
PubMed reference number	17850084
Journal	Medline
Volume Number	129
Issue Number	39
Alternate Webpage(s)	http://collum.chem.cornell.edu/publications/102_SI.pdf
Alternate Webpage(s)	http://collum.chem.cornell.edu/publications/102.pdf
Journal	Journal of the American Chemical Society
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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