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1 article(s) from Ortegón-Reyna, David

Investigation of the role of stereoelectronic effects in the conformation of piperidones by NMR spectroscopy and X-ray diffraction

Cesar Garcias-Morales,
David Ortegón-Reyna and
Armando Ariza-Castolo

Beilstein J. Org. Chem. 2015, 11, 1973–1984, doi:10.3762/bjoc.11.213

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Figure 1: (a) Schematic representation of the vicinal σ_C−H→σ*_C−X interaction by double-bond/no-bond resonance...

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Figure 2: Schematic representation of stereoelectronic effects (a) hyperconjugation, (b) homohyperconjugation...

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Figure 3: Schematic representation of possible homoanomeric interactions in six-membered saturated heterocycl...

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Figure 4: Structure of compounds 1 to 8.

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Scheme 1: Proposed reaction mechanism for the synthesis of piperidones by the Mannich reaction. The substitue...

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Scheme 2: For 6, R¹ = R² = H, for 7, R¹ = H, R² = CH₃, for 8, R¹ = R² = CH₃.

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Figure 5: (a) Favored conformation for compound 1, determined by nOe effect, (b) t-ROESY spectrum of 1 record...

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Figure 6: (a) Preferred conformation of 4 determined by nOe, (b) t-ROESY spectrum of 4 recorded at 500 MHz in...

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Figure 7: (a) ORTEP diagram of 1. The thermal ellipsoids are drawn at the 30% probability level for all atoms...

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Figure 8: (a) ORTEP diagrams of 6 and 7. The thermal ellipsoids are drawn at the 30% probability level for al...

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Figure 9: (a) ¹J_C,H coupling constant of 3, 5, 6, and 8. (b) Plot of the population analysis versus ¹J_C,H (sl...

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Scheme 3: Representation of the n_N→σ*_C–H(7)eq interaction. The interaction energy is 0.55 kcal/mol at the ωB9...

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Figure 10: Distances between N(3) and C(7) for 3, 5, 6, and 7 measured in the structures obtained by XRD.

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Published 22 Oct 2015

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