Acid-catalyzed transannular cyclization of medium ring unsaturated sulfides. The effect of ring size and double bond geometry on rate

V Cerè, F Peri, S Pollicino, A Antonio

Index: Cere, Vanda; Peri, Francesca; Pollicino, Salvatore; Antonio, Arcelli Journal of the Chemical Society. Perkin Transactions 2, 1998 , # 4 p. 977 - 979

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Abstract

The acid-catalyzed transannular cyclization of 8–10-membered γ, δ-unsaturated cyclic sulfides yields cis fused bicyclic sulfonium salts independently of the geometry of the double bond. The rate varies linearly with the acidity function–(H0) I with a slope of 1. The rate variations span about six powers of ten range, the maximum rate difference being observed for the E/Z thiacyclooct-4-ene pair. The data are consistent with the classical interpretation ...