17O NMR Spectra of Divinyl Ethers

Taskinen, Esko

doi:10.1002/(sici)1097-458x(199702)35:2<107::aid-omr26>3.0.co;2-y

Cited by 15 publications

(2 citation statements)

References 24 publications

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“…on the nature, number and position of substituents attached to the -O-C=C. According to previous work of Taskinen et al[19][20], substituent's bulkiness plays an important role in the spatial orientation of the -O-C=C system and therefore, in its polarization degree. In summary, the strength of p- conjugation in vinyl ethers depends on several structural factors, such as the stereochemistry of the C-O-C=C fragment and the electronic nature of substituents attached to the -carbon of the vinyl group.…”

mentioning

confidence: 96%

UV absorption cross-sections of a series of vinyl ethers

Nieto-Gligorovski¹,

Gligorovski²,

Romanò³

et al. 2009

Journal of Photochemistry and Photobiology A: Chemistry

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confidence: 96%

UV absorption cross-sections of a series of vinyl ethers

Nieto-Gligorovski¹,

Gligorovski²,

Romanò³

et al. 2009

Journal of Photochemistry and Photobiology A: Chemistry

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“…Divinyl ethers such as 1 are important raw materials, primarily for the production of vinyl polymeric materials containing oxygen bridges which are expected to be biodegradable in nature 1 2 3 . Divinyl ether itself has rather unique thermodynamic and spectroscopic properties 4 5 6 7 8 and it was first prepared by the exhaustive methylation of morpholine by Knorr and Matthes in 1899 9 . Because the synthetic reaction was performed under harsh conditions in low yields, much efforts have been devoted to the efficient preparation of those divinyl ethers.…”

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confidence: 99%

Unprecedented reactions: from epichlorohydrin to epoxyglycidyl substituted divinyl ether and its conversion into epoxyglycidyl propargyl ether

Yao

Qiu

et al. 2015

Sci Rep

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The reaction of epichlorohydrin with concentrated sodium hydroxide in hexane under phase transfer conditions has surprisingly led to the formation of the symmetrical di(3-epoxyglycidyl-1-propenyl) ether 1 which contains both nucleophilic and electrophilic moieties. When it was reacted with n-butyllithium, intermediate 1 once again surprisingly generated epoxyglycidyl propargyl ether, which was further reacted in situ with a variety of benzaldehydes to furnish the corresponding substituted propargylic alcohols in good yields. While the reaction is operationally simple, it provides a powerful method for the synthesis of the important products from commodity materials such as epichlorohydrin. Moreover, these reactions may have revealed that some fundamental properties of the hydroxide anion in those once thought straightforward reactions are not well understood. A careful analysis of the experimental data suggests that an unprecedented concerted elimination of the epoxyglycidyl ether with sodium hydroxide may be operative and an alpha deprotonation followed by alpha elimination of the di(3-epoxyglycidyl-1-propenyl) ether with alkyllithium may have been involved.

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Characterization of 2,5‐diaryl‐1,3,4‐oxadiazolines by multinuclear magnetic resonance and density functional theory calculations. Investigation on a case of very remote Hammett correlation

Cerioni¹,

Maccioni

Cardia

et al. 2009

Magnetic Reson in Chemistry

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Two series of 2,5-diaryl-1,3,4-oxadiazolines have been studied by multinuclear magnetic resonance and density functional theory calculations. A full NMR spectroscopic characterization has been performed and excellent remote Hammett correlations (sigma(p) or sigma(p)+) have been found for para substitution in the two aryl rings through at least 11 bonds, notwithstanding the presence in the path of atoms that should act as insulators and a lack of correlation for some of the intermediate atoms. The computational investigation on the electronic delocalization, performed with the ACID (anisotropy of the induced current density) method, reveals indeed that electrons are delocalized in almost the entire molecule despite the presence of the insulators.

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17O NMR Spectra of Divinyl Ethers

Cited by 15 publications

References 24 publications

UV absorption cross-sections of a series of vinyl ethers

UV absorption cross-sections of a series of vinyl ethers

Unprecedented reactions: from epichlorohydrin to epoxyglycidyl substituted divinyl ether and its conversion into epoxyglycidyl propargyl ether

Characterization of 2,5‐diaryl‐1,3,4‐oxadiazolines by multinuclear magnetic resonance and density functional theory calculations. Investigation on a case of very remote Hammett correlation

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