Nucleophilic reactivity of sulfonyl oxygen. Detection and isolation of γ-sultinium ions

Abstract

The addition of Cl₂, Br₂ or lCl to 2-endo-3-exo-bis(phenylsulfonyl)norborn-5-ene 1 in the presence of AgBF₄, or the methylation of the epoxide of 1 allow the observation or isolation of the isomeric γ-sultinium ions 2 and 3(X = Cl, Br, I, OMe); the addition of Me₃S₃⁺SbCl₆^– leads to thiiranium ion 4(X = SMe); in the case of X = 1, 2 and 3 interconvert via the intermediacy of 4.