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Issue 19, 1999
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Synthesis of cyclic ethers and allylic sulfides by rearrangement of phenylsulfanyl substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride

Abstract

Rearrangement of a series of 1,n-diols (n = 2 to 12), with a PhS-group adjacent to one OH group, under two sets of conditions gives single compounds in excellent yield drawn for four possible classes of products. The effect of the chain length helps in the understanding of the different cyclisation modes and the mechanism of the rearrangements.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1999, 2771-2782
Article type
Paper

Synthesis of cyclic ethers and allylic sulfides by rearrangement of phenylsulfanyl substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride

L. Djakovitch, J. Eames, D. J. Fox, F. H. Sansbury and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1999, 2771
DOI: 10.1039/A905498G

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