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DOI: 10.1039/A705457B (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 977-980

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

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Vanda Cerè, Francesca Peri, Salvatore Pollicino and Arcelli Antonio

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 of the intramolecular reactivity in terms of internal strain of the substrate and/or of the transition state.

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