Solvents of Low Nucleophilicity. VIII. Possible Vinyl Cation Intermediates, a 1, 4-Chlorine Shift, and Novel Substituent Cleavages in the Reaction of Trifluoroacetic Acid …

PE Peterson, JE Duddey

Index: Peterson,P.E.; Duddey,J.E. Journal of the American Chemical Society, 1966 , vol. 88, p. 4990 - 4996

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Citation Number: 28

Abstract

Abstract: The reactions of trifluoroacetic acid with unsubstituted hexynes and with 5- substituted 1-pentynes having chloro, methoxy, acetoxy, trifluoroacetoxy, and cyano substituents occurred readily at rates comparable to those previously determined for the corresponding alkenes. One mole of trifluoroacetic acid added nonstereospecifically to 3- hexyne) presumably via a vinyl cation intermediate, to give cis-and trans-3-hexen-3-yl ...

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Mechanistic and synthetic aspects of the acid-catalysed hydr...

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