Original scientific paper

The Formation of Cyclic Ethers from Olefinic Alcohols Part XI*. The Oxidative Cyclization of Some Open-Chain Unsaturated Alcohols by Means of Organic Peracids

Mihailo Lj. Mihailović ; Department of Chemistry, Faculty of Science, University of Belgrade, and Institute of Chemistry, Technology and Metallurgy, Bellgrade, P. O. box 550, 11001 Belgrade, Serbia, Yugoslavia
Dragan Marinković ; Department of Chemistry, Faculty of Science, University of Belgrade, and Institute of Chemistry, Technology and Metallurgy, Bellgrade, P. O. box 550, 11001 Belgrade, Serbia, Yugoslavia

Abstract

Reactions of some acyclic olefinic alcohols with organic peracids (mainly 3-chloroperbenzoic acid) have been studied. It was found that L'.3-alkenols, with one exception (4-methyl-3- penten-1-ol), do not cyclize, whereas L'.4-alkenols afford cyclic hydroxyethers, the ratio of five- to six-membered ring products depending mostly upon the number and position of methyl (alkyl) substituents at the double bond and at the carbinol carbon atom, and varying from 100: O to 57.5: 42.5. L'.5-alkenols give six-rmembered cyclic hydroxy-ethers, whereas L'.6- and L'.7-alkenols do not cyclize. The alkaline hydrolysis (in aqueous sodium hydroxide) of epoxy-acetates derived from L'.4-alkenols affords also cyclic hydroxy-ethers, the five- to six-membered ring ratio varying from 100: O to 67: 33, whereas basic hydrolysis of 1-acetoxy-5,6-epoxyhexane gives a mixture of six- and seven-membered cyclic hydroxy-ethers.

Keywords

Hrčak ID:

177581

URI

https://hrcak.srce.hr/177581

Publication date:

16.5.1986.

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