Tetrahedron

Formation of cyclic sulfonium salts by Me 3 SiI-promoted intramolecular displacement of hydroxide or methoxide by sulfide. Ring contraction thiepane→ thiolane

V Cere, S Pollicino, A Fava

文献索引：Cere, Vanda; Pollicino, Salvatore; Fava, Antonino Tetrahedron, 1996 , vol. 52, # 16 p. 5989 - 5998

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被引用次数: 10

摘要

A suitably positioned (1, 2-, 1, 4-, and 1, 5-) intramolecular sulfide interferes with the iodotrimethylsilane-promoted iodine for hydroxyl substitution, as well as the related alcohol deprotection procedure (regioselective cleavage of methyl ethers). The outcome may be a cyclic sulfonium salt or an iodide arising from cleavage of a sulfonium intermediate. Cyclization is especially favored with secondary and tertiary alcohols or ethers, and with ...