A 13C-NMR study of squalene, part II : functionalized squalene-like compounds

M.E. van Dommelen; L.J.M. Ven, van de; H.M. Buck; J.W. Haan, de

doi:10.1002/recl.19770961203

A 13C-NMR study of squalene, part II : functionalized squalene-like compounds

M.E. van Dommelen, L.J.M. Ven, van de, H.M. Buck, J.W. Haan, de

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Abstract

13C-NMR chemical shifts of substituted squalenes and model compounds with a heteroatom in d-position to a double bond show that a steric interaction exists between the hetero-atom and the double bond. This points to the presence of "precoiled" conformations in the hetero-substituted squalenes and also in squalene itself. The nature of the interaction remains veiled, but it appears to be a general feature as is shown in a series of 2- and 3-substituted thiophenes with a double bond in the side chain.

Original language	English
Pages (from-to)	295-301
Journal	Recueil des Travaux Chimiques des Pays-Bas
Volume	96
Issue number	12
DOIs	https://doi.org/10.1002/recl.19770961203
Publication status	Published - 1977

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abstract = "13C-NMR chemical shifts of substituted squalenes and model compounds with a heteroatom in d-position to a double bond show that a steric interaction exists between the hetero-atom and the double bond. This points to the presence of {"}precoiled{"} conformations in the hetero-substituted squalenes and also in squalene itself. The nature of the interaction remains veiled, but it appears to be a general feature as is shown in a series of 2- and 3-substituted thiophenes with a double bond in the side chain.",

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AU - Haan, de, J.W.

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N2 - 13C-NMR chemical shifts of substituted squalenes and model compounds with a heteroatom in d-position to a double bond show that a steric interaction exists between the hetero-atom and the double bond. This points to the presence of "precoiled" conformations in the hetero-substituted squalenes and also in squalene itself. The nature of the interaction remains veiled, but it appears to be a general feature as is shown in a series of 2- and 3-substituted thiophenes with a double bond in the side chain.

AB - 13C-NMR chemical shifts of substituted squalenes and model compounds with a heteroatom in d-position to a double bond show that a steric interaction exists between the hetero-atom and the double bond. This points to the presence of "precoiled" conformations in the hetero-substituted squalenes and also in squalene itself. The nature of the interaction remains veiled, but it appears to be a general feature as is shown in a series of 2- and 3-substituted thiophenes with a double bond in the side chain.

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DO - 10.1002/recl.19770961203

M3 - Article

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JF - Recueil des Travaux Chimiques des Pays-Bas

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ER -

A 13C-NMR study of squalene, part II : functionalized squalene-like compounds

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