Superacid-Catalyzed electrocyclization of diphenylmethyl cations to fluorenes. kinetic and theoretical revisit supporting the involvement of ethylene dications

T Ohwada, T Suzuki, K Shudo

Index: Ohwada, Tomohiko; Suzuki, Takayoshi; Shudo, Koichi Journal of the American Chemical Society, 1998 , vol. 120, # 19 p. 4629 - 4637

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Citation Number: 32

Abstract

In superacid media, diphenylmethyl cations bearing an α-carbonyl group generate fluorene compounds. We have obtained chemical evidence showing the acidity dependence of this fluorene cyclization process. A linear relationship was found between the rate of the fluorene cyclization and the acidity of the reaction media in kinetic studies, strongly supporting the intervention of an additional proton transfer to the diphenylmethyl monocation in the ...

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