Solvolysis of ethenoanthracenyl triflates. Novel stabilized cyclic vinyl cations

…, PJ Stang, MD Schiavelli, MH Kowalski

Index: Ladika, Mladen; Stang, Peter J.; Schiavelli, Melvyn D.; Kowalski, Mark H. Journal of the American Chemical Society, 1984 , vol. 106, # 21 p. 6372 - 6375

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Citation Number: 2

Abstract

Abstract: The solvolytic behavior of ethenoanthracenyl (3a) and etheno-9, lO- dimethylanthracenyl (3b) triflates was examined. Despite the strain inherent in these systems, 3a reacts lo5 times faster than cyclohexenyl triflate and 11 times faster than the unstrained cis-Zbutenyl triflate. These results are explained by an unusual aryl stabilization of the incipient vinyl cations.