Solvolysis of 2-Adamantyl Trifluoromethanesulfonate : A YOTf Scale

Article abstract of DOI:10.1021/jo00218a017

The solvolysis of 2-adamantyl trifluoromethanesulfonate proceeds at a convenient rate at temperatures below ambient in a wide variety of pure and aqueous organic solvents and in ethanol-2,2,2-trifluoroethanol mixtures.A scale of Grunwald-Winstein Y values (Y_OTf) is developed for 26 solvents and it is found to much more closely resemble the corresponding y_OClO3 scale than the corresponding scale of Y_OTs values.In aqueous ethanol, there is a preference for product formation by interaction with water molecules by a factor of ca. 1.5, essentially independent of solvent composition (96-50percent ethanol).