Tetrahedron letters

para-toluenesulfonyl iodide as a convenient, mild reagent for the preparation of functionalised cyclic ethers

GL Edwards, KA Walker

Index: Edwards, Gavin L.; Walker, Katherine A. Tetrahedron Letters, 1992 , vol. 33, # 13 p. 1779 - 1782

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Citation Number: 6

Abstract

Abstract Free radical addition of para-toluenesulfonyl iodide to alkenols occurs readily to give functionalised β-iodosulfones as single regioisomers. Cyclisation to give cyclic ethers is effected by treatment with potassium carbonate in methanol. An anomalous reaction, where a substituted alkenol cyclises directly to give an iodotetrahydropyran, is also discussed.