Superacid-catalyzed electrocyclization of 1-phenyl-2-propen-1-ones to 1-indanones. Kinetic and theoretical studies of electrocyclization of oxonium-carbenium …

T Suzuki, T Ohwada, K Shudo

Index: Suzuki, Takayoshi; Ohwada, Tomohiko; Shudo, Koichi Journal of the American Chemical Society, 1997 , vol. 119, # 29 p. 6774 - 6780

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Citation Number: 78

Abstract

Strongly acidic conditions are required to induce the Nazarov-type cyclization of aryl vinyl ketones, although chemical analogy with the Nazarov reaction would superficially imply a straightforward electrocyclization reaction of the O-protonated monocation. In this paper we describe the superacid-catalyzed prototype cyclization of 1-phenyl-2-propen-1-ones. The acidity dependence of these cyclization reactions as revealed by kinetic measurements ...

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