Solvolyses of 2. alpha., 5-epithio-5. alpha.-and-epoxy-5. alpha.-cholestane derivatives. A reactivity factor of 1011 due to sulfur participation in a 7-thiabicyclo [2.2. 1] …

H Tanida, T Tsuji, T Komeno, H Itani

Index: Tsuji,T. et al. Journal of Organic Chemistry, 1971 , vol. 36, # 12 p. 1648 - 1653

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Abstract

Solvolysis reactions of 2aJ5-epithio-5a-cholestanes, a corresponding sulfoxide, and 2aJ5- epoxy-5a-cholestanes bearing a bromo or methanesulfonyloxy group at the C-3 exo (a) or endo (0) reaction site were investigated in aqueous dioxane and compared with the solvolyses of ero-and endo-2-norbornyl methanesulfonates (12 and 13). Rates of exo derivatives of the epithiocholestane (6), the epoxycholestane (9), and 7-oxabicyclo [2.2. 1] ...