DIFFERENTIAL BRIDGING IN THE SOLVOLYSIS OF 6- AND 7-SUBSTITUTED 2-EXO- AND 2-ENDO-NORBORNYL p-TOLUENESULFONATES

Article abstract of DOI:10.1016/S0040-4039(00)88133-2

The large difference between the reaction constants ρ_I for the solvolysis of the 6-exo- and 7-anti-substituted norbornyl tosylates 3 and 7, respectively, is further proof for the hypothesis that 2-norbornyl cations are anisotropic with regard to the transmission of polar effects and that through space induction involves graded bridging.