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Conformational studies by dynamic NMR. Part 56. Enantiotopomerization and conformational analysis of hindered aryl alkyl ketones investigated by dynamic and solid state NMR

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
52
Issue
7
Identifiers
DOI: 10.1016/0040-4020(95)01068-8

Abstract

Abstract The barriers (ΔG ∗) for the degenerate interconversion (enantiotopomerization) of a number of mesityl alkyl ketones have been measured by dynamic NMR in a chiral environment. These barriers were compared with those of more hindered ketones having the three methyl groups of the mesityl moiety replaced by three isopropyl groups. These prochiral probes allowed the barriers to be determinated in achiral solvents. The conformations were also assessed by high resolution solid state 13C NMR and Molecular Mechanics calculations.

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