Highly activated vinyl hydrogen in a significantly twisted styrene

…, T Matsuo, Y Yoshioka, S Katsumura

Index: Mori, Hajime; Matsuo, Takafumi; Yoshioka, Yasunori; Katsumura, Shigeo Journal of Organic Chemistry, 2006 , vol. 71, # 24 p. 9004 - 9012

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Citation Number: 13

Abstract

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 ...