Journal of the American Chemical Society

Neighboring Carbon and Hydrogen. XI. Solvolysis of exo-Norbornyl p-Bromobenzenesulfonate1, 2, 3

S Winstein, D Trifan

Index: Winstein; Trifan Journal of the American Chemical Society, 1952 , vol. 74, p. 1154,1159 Journal of the American Chemical Society, 1949 , vol. 71, p. 2953

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Citation Number: 161

Abstract

! I1 F1 useful quantities of exo-norborneol (11)'anh its derivatives. The solvolysis of exo- norbornyl p-bromobenzenesulfonate (111), as in the case of the endo-isomer, 6 gave rise essentially exclusively to exo-products. Thus the acetolysis product IV (obtainable in SOYo yield) was at least 94% exo, as shown by infrared spectrum6 (Fig. l), refractive index, 6 and saponification and conversion to the 3, s-dinitrobenzoate. In the case of solvolysis in 75% ...