Lithiated imines: solvent-dependent aggregate structures and mechanisms of alkylation.

Journal of the American Chemical Society
Stephan J ZuendDavid B Collum

Abstract

We describe efforts to understand the structure and reactivity of lithiated cyclohexanone N-cyclohexylimine. The lithioimine affords complex solvent-dependent distributions of monomers, dimers, and trimers in a number of ethereal solvents. Careful selection of solvent provides exclusively monosolvated dimers. Rate studies on the C-alkylations reveal chronic mixtures of monomer- and dimer-based pathways. We explore the factors influencing reactants and alkylation transition structures and the marked differences between lithioimines and isostructural lithium dialkylamides with the aid of density functional theory calculations.

References

Jul 18, 2001·Journal of the American Chemical Society·J L Rutherford, D B Collum
Feb 15, 2003·The Journal of Organic Chemistry·Olivier PariselClaude Giessner-Prettre
Dec 5, 2003·Journal of the American Chemical Society·Songping Liao, David B Collum
Dec 18, 2003·Journal of the American Chemical Society·Sean H WiedemannDavid B Collum
Mar 12, 2004·Journal of the American Chemical Society·Pinjing ZhaoDavid B Collum
May 13, 2004·Chemical Reviews·Sven MangelinckxNorbert De Kimpe

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Citations

Jul 5, 2011·Journal of the American Chemical Society·Brian M Casey, Robert A Flowers
Oct 5, 2010·Organic Letters·Eugene E Kwan, David A Evans
May 18, 2016·Organic & Biomolecular Chemistry·Ying-Ying SongChu-Yi Yu
Jan 17, 2007·Chemistry : a European Journal·Aurélien de la LandeOlivier Parisel
Feb 4, 2010·Journal of the American Chemical Society·Hassan K KhartabilManuel F Ruiz-López
Oct 29, 2008·The Journal of Organic Chemistry·Hassan K KhartabilManuel F Ruiz-López
May 12, 2009·The Journal of Physical Chemistry. a·Bart De SterckMichel Waroquier

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