Issue 12, 2000

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

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.

Article information

Article type
Paper
Submitted
24 Nov 1999
Accepted
13 Apr 2000
First published
25 May 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1815-1827

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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