Tetrahedron

Lead tetraacetate oxidation of saturated aliphatic alcohols—IV: The formation of six-membered cyclic ethers

ML Mihailović, Ž C̆eković, D Jeremić

Index: Mihailovic,M.L. et al. Tetrahedron, 1965 , vol. 21, p. 2813 - 2821

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Citation Number: 21

Abstract

The lead tetraacetate oxidation of saturated aliphatic alcohols, with structures which do not permit 1, 5-cyclization, gave tetrahydropyran derivatives in yields not exceeding 16%. The formation of a small amount of the rearranged ether, 2-ethyl-2-methyltetrahydrofuran, from 4, 4-dimethyl-1-pentanol indicates that the cyclization reaction proceeds via an intermediate with carbonium ion character.