Journal of the American Chemical Society

Vinyl cations. 12. Mechanism of reaction of cis-and trans-3-phenyl-2-buten-2-yl triflates. Evidence for vinylidene phenonium ions

PJ Stang, TE Dueber

Index: Stang,P.J.; Dueber,T.E. Journal of the American Chemical Society, 1977 , vol. 99, # 8 p. 2602 - 2610

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Citation Number: 21

Abstract

Abstract: The solvolyses of a series of ring substituted cis-and trans-3-phenyl-2-buten-2-yl triflates were investigated in CF3CH2OH. The vinyl triflates were prepared from the corresponding 3-aryl-2-butanones. The p value for reaction of the E triflates was found to be p=-3.76 and for the corresponding Z isomers p=-1.96 in 97% aqueous TFE at 100 OC. A Taft u* correlation gave ap*=-6.4 with the rates for the 2 isomers falling on the same line as the ...

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