Dynamic <sup>13</sup>C NMR study of the cyclohexane ring in spirocyclohexanes

Iratçabal, P.; Grenier‐Loustalot, Marie‐Florence; Lichanot, Albert; Metras, F.

doi:10.1002/mrc.1270140606

Cited by 8 publications

(1 citation statement)

References 18 publications

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“…Compounds 1a 21 to 1c show a chemical exchange between axial and equatorial positions that was demonstrated previously. 19,21 Furthermore, the imine-diazolidine tautomeric equilibrium was analyzed.…”

Section: Introductionmentioning

confidence: 53%

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR

Guerrero‐Álvarez

Moncayo-Bautista

Ariza‐Castolo

2004

Magnetic Reson in Chemistry

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The relative configuration of 11 1,4-diazaspiro[4.5]decanes (1a-1j and 1m), 15 1,4-oxazaspiro[4.5]decanes (2a-2o) and 10 1,4-dioxaspiro[4.5]decanes (3a-3n) substituted at the 2-, 6-, 7- or 8-position by a methyl group or using the tert-butyl group as a model for the ananchomeric structure is reported. The relative stereochemistry was analyzed by 1H, 13C, 15N and 17O NMR and all isomers present were characterized spectroscopically. Compounds with a methyl group in the six-membered ring show a chair conformation preference with the methyl group in the equatorial position. Compounds with one or two nitrogens exhibit a tautomeric equilibrium between the imine-diazolidine forms, as demonstrated by IR and 13C NMR.

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Section: Introductionmentioning

confidence: 53%

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR

Guerrero‐Álvarez

Moncayo-Bautista

Ariza‐Castolo

2004

Magnetic Reson in Chemistry

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Stereochemical arrangement of spiro[4.5]decane derivatives by15N and17O NMR spectroscopy

Ariza‐Castolo

Godoy-Reyes

1999

Magn. Reson. Chem.

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The relative axial–equatorial position of spiro[4.5]decanes substituted in the 1,4‐positions by oxygen or nitrogen were assigned by 15N and 17 O NMR spectroscopy. The substituent, chemical exchange and steric effects upon the chemical shifts are discussed. A linear relationship between 15N and 17O was found and the relative configuration of the chiral spiro atom was determined. Copyright © 1999 John Wiley & Sons. Ltd.

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Conformational Dynamics of 9,9‐Dimethyl‐1,5‐Dihetero‐Spiro [5.5] Undecanes by Molecular Mechanics Calculations: A Three‐Dimensional Topological Approach

Iratçabal

Liotard

1986

J Comput Chem

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The dynamic behavior of 9,9-dimethyl-l,5-dihetero-spiro [5.5] undecanes is investigated by molecular mechanics calculations. A topological approach is taken which leads to a model consistent with the available NMR data. A three-dimensional representation of the conformational potential energy surface is given.*The historically first-defined mathematical term "critical point of index i''7e will be used in this study instead of "i -dimensional partial maximum",3g~4d or less precise terms like "stationary point," "super saddle point," etc. The index of a critical point is defined in the computational details section.

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Dynamic ¹³C NMR study of the cyclohexane ring in spirocyclohexanes

Abstract: A dynamic study of spirocyclohexanes was carried out using low-temperature 13C nuclear magnetic resonance spectroscopy. The variations of the energy barrier to inversion of the cyclohexane ring are interpreted in the spiro substituent. terms of the electronegativity of the heteroatoms of

Cited by 8 publications

References 18 publications

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR

Stereochemical arrangement of spiro[4.5]decane derivatives by15N and17O NMR spectroscopy

Conformational Dynamics of 9,9‐Dimethyl‐1,5‐Dihetero‐Spiro [5.5] Undecanes by Molecular Mechanics Calculations: A Three‐Dimensional Topological Approach

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Dynamic 13C NMR study of the cyclohexane ring in spirocyclohexanes

Abstract: A dynamic study of spirocyclohexanes was carried out using low-temperature 13C nuclear magnetic resonance spectroscopy. The variations of the energy barrier to inversion of the cyclohexane ring are interpreted in the spiro substituent. terms of the electronegativity of the heteroatoms of

Cited by 8 publications

References 18 publications

Assignment of the relative configuration of spiro[4.5]decanes by 13C, 15N and 17O NMR

Assignment of the relative configuration of spiro[4.5]decanes by 13C, 15N and 17O NMR

Stereochemical arrangement of spiro[4.5]decane derivatives by15N and17O NMR spectroscopy

Conformational Dynamics of 9,9‐Dimethyl‐1,5‐Dihetero‐Spiro [5.5] Undecanes by Molecular Mechanics Calculations: A Three‐Dimensional Topological Approach

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Dynamic ¹³C NMR study of the cyclohexane ring in spirocyclohexanes

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR