Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene

The novel example of a vinylic hydrogen more reactive than a benzylic hydrogen was found by treatment of a twisted styrene derivative with a strong base followed by D2O quenching. In this paper, the full details of the examples of the highly activated vinyl hydrogens in twisted styrene derivatives are described, with a discussion on the correlation between the reactivity of the vinyl hydrogens and the magnitude of the twist. The highly reactive vinyl hydrogens could be rationalized by considering the novel orbital interaction between the π* orbital of the benzene ring and the σ orbital of the vinylic C−H bond in the twisted styrene derivatives.

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PID https://www.doi.org/10.1021/jo061092z.s001
URL https://figshare.com/articles/dataset/Highly_Activated_Vinyl_Hydrogen_in_a_Significantly_Twisted_Styrene/3045850
URL http://dx.doi.org/10.1021/jo061092z.s001
URL https://figshare.com/articles/Highly_Activated_Vinyl_Hydrogen_in_a_Significantly_Twisted_Styrene/3045850
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Access Right Open Access
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Author Mori, Hajime
Author Matsuo, Takafumi
Author Yoshioka, Yasunori
Author Katsumura, Shigeo
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Collected From figshare
Hosted By figshare
Publication Date 2016-01-01
Publisher Figshare
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Language UNKNOWN
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keyword arxiv.Physics::Chemical Physics
system:type dataset
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Source https://science-innovation-policy.openaire.eu/search/dataset?datasetId=r37980778c78::165d7457326e44c643ce4f73d187dd2a
Author jsonws_user
Last Updated 12 January 2021, 16:34 (CET)
Created 12 January 2021, 16:34 (CET)