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

MF Buffet, DJ Dixon, GL Edwards, SV Ley…

Index: Buffet, Marianne F.; Dixon, Darren J.; Edwards, Gavin L.; Ley, Steven V.; Tate, Edward W. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 12 p. 1815 - 1827

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Citation Number: 16

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 2 H incorporated into the side chain and ring system it is proposed that these reactions proceed via an intermolecular pathway.