Beilstein J. Org. Chem.2017,13, 1781–1787, doi:10.3762/bjoc.13.172
physicochemical/biological property of interest. In this work, structural changes in 2-fluorocyclohexanone were theoretically studied with the aim at finding intramolecular interactions that induce the conformational equilibrium towards the axial or equatorial conformer. The interactions evaluated were hydrogen
compounds. Spectroscopic parameters (NMR chemical shifts and coupling constants), which can be useful to determine the stereochemistry and the interactions operating in the series of 2-fluorocyclohexanone derivatives, were also calculated.
Keywords: classical effects; conformational analysis; 2
interaction with the carbonyl oxygen or by electron delocalization (hyperconjugation) involving the good electron acceptor π*C=O orbital. For example, 2-fluorocyclohexanone in the gas phase exists predominantly in the axial conformation, but the equatorial form is more stable in solution [18]. In a previous
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Graphical Abstract
Figure 1:
2-Fluorocyclohexanone (X = CH2 and Y = O) derivatives (X and Y = CH2, NH, O or S).
Beilstein J. Org. Chem.2016,12, 1647–1748, doi:10.3762/bjoc.12.162
(Scheme 29) [270].
In most cases, the Baeyer–Villiger oxidation is a stereospecific and regioselective process with retention of the configuration. The oxidation of cis-4-tert-butyl-2-fluorocyclohexanone (93) with m-chloroperbenzoic acid in the presence of NaHCO3 affords fluorolactones 94 and 95 in 91
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Graphical Abstract
Figure 1:
The named transformations considered in this review.