American Chemical Society
jo061092z_si_002.pdf (6.27 MB)

Highly Activated Vinyl Hydrogen in a Significantly Twisted Styrene

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journal contribution
posted on 2006-11-24, 00:00 authored by Hajime Mori, Takafumi Matsuo, Yasunori Yoshioka, Shigeo Katsumura
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.