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

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