Tetrahedron letters

Differential bridging in the solvolysis of 6-and 7-substituted 2-exo and 2-endo-norbornyl p-toluenesulfonates

P Flury, CA Grob

Index: Flury, Peter; Grob, Cyril A. Tetrahedron Letters, 1983 , vol. 24, # 31 p. 3195 - 3198

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Abstract

The large difference between the reaction constants p I for the solvolysis of the 6-exo- and 7-anti-substituted norbornyl tosylates and , 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. ... Helv. Chim. Acta, 65 (1982), p. 1720 and earlier papers cited therein. ... , and are somewhat larger in trifluoroethanol than in 80 % ...