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Issue 12, 2000
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Oxygen to carbon rearrangements of anomerically linked alkenols from tetrahydropyran derivatives: an investigation of the reaction mechanism via a double isotopic labelling crossover study

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Abstract

A variety of alkenol tetrahydropyran derivatives were prepared and subjected to a tin tetrachloride promoted anomeric oxygen to carbon rearrangement. Using this methodology many of the corresponding carbon-linked structures were synthesised, including alkenes and bicyclic ethers, in good yields. On the basis of an isotopic labelling study using 2H incorporated into the side chain and ring system it is proposed that these reactions proceed via an intermolecular pathway.

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Publication details

The article was received on 24 Nov 1999, accepted on 13 Apr 2000 and first published on 25 May 2000


Article type: Paper
DOI: 10.1039/A909300A
Citation: J. Chem. Soc., Perkin Trans. 1, 2000, 1815-1827
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    Oxygen to carbon rearrangements of anomerically linked alkenols from tetrahydropyran derivatives: an investigation of the reaction mechanism via a double isotopic labelling crossover study

    M. F. Buffet, D. J. Dixon, G. L. Edwards, S. V. Ley and E. W. Tate, J. Chem. Soc., Perkin Trans. 1, 2000, 1815
    DOI: 10.1039/A909300A

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