Stereoelectronic effects in force-accelerated retro-Diels–Alder reactionsCitation formats

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Stereoelectronic effects in force-accelerated retro-Diels–Alder reactions. / Wu, Lik Chun; De Bo, Guillaume.

In: SYNLETT, 03.2022.

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@article{060880fe7d46456d93a23eec15fc29bf,
title = "Stereoelectronic effects in force-accelerated retro-Diels–Alder reactions",
abstract = "In polymer mechanochemistry, mechanosensitive molecules(mechanophores) are activated upon elongation of anchored polymer arms. The reactivity of a mechanophore can be influenced by a variety of structural factors, including the geometry of attachment of the polymer arms and the nature of eventual substituents. Here we investigate stereoelectronic effects in force-accelerated Diels–Alder reactions using the CoGEF (Constrained Geometries simulate External Force) calculation method. We found that the presence of an electron-donating heteroatom on the diene leads to a lower activation force, and that the mechanochemical reactivity is suppressed when the anchor group is attached to a central rather than lateral position.",
keywords = "Polymer mechanochemistry, mechanophore, force, Diels–Alder, retrocycloaddition, Hammett parameter",
author = "Wu, {Lik Chun} and {De Bo}, Guillaume",
year = "2022",
month = mar,
doi = "10.1055/a-1799-7517",
language = "English",
journal = "SYNLETT",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",

}

RIS

TY - JOUR

T1 - Stereoelectronic effects in force-accelerated retro-Diels–Alder reactions

AU - Wu, Lik Chun

AU - De Bo, Guillaume

PY - 2022/3

Y1 - 2022/3

N2 - In polymer mechanochemistry, mechanosensitive molecules(mechanophores) are activated upon elongation of anchored polymer arms. The reactivity of a mechanophore can be influenced by a variety of structural factors, including the geometry of attachment of the polymer arms and the nature of eventual substituents. Here we investigate stereoelectronic effects in force-accelerated Diels–Alder reactions using the CoGEF (Constrained Geometries simulate External Force) calculation method. We found that the presence of an electron-donating heteroatom on the diene leads to a lower activation force, and that the mechanochemical reactivity is suppressed when the anchor group is attached to a central rather than lateral position.

AB - In polymer mechanochemistry, mechanosensitive molecules(mechanophores) are activated upon elongation of anchored polymer arms. The reactivity of a mechanophore can be influenced by a variety of structural factors, including the geometry of attachment of the polymer arms and the nature of eventual substituents. Here we investigate stereoelectronic effects in force-accelerated Diels–Alder reactions using the CoGEF (Constrained Geometries simulate External Force) calculation method. We found that the presence of an electron-donating heteroatom on the diene leads to a lower activation force, and that the mechanochemical reactivity is suppressed when the anchor group is attached to a central rather than lateral position.

KW - Polymer mechanochemistry

KW - mechanophore

KW - force

KW - Diels–Alder

KW - retrocycloaddition

KW - Hammett parameter

UR - https://www.thieme-connect.com/products/ejournals/abstract/10.1055/a-1799-7517

U2 - 10.1055/a-1799-7517

DO - 10.1055/a-1799-7517

M3 - Letter

JO - SYNLETT

JF - SYNLETT

SN - 0936-5214

ER -