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

Content Provider	Semantic Scholar
Author	Marinković, Dragan
Copyright Year	2017
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 fiveto 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-rnembered cyclic hydroxy-ethers, whereas L'.6and 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 fiveto six-membered ring ratio varying from 100: O to 67: 33, whereas basic hydrolysis of l-acetoxy-5,6-epoxyhexane gives a mixture of sixand seven-membered cyclic hydroxy-ethers.
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://hrcak.srce.hr/file/261761
Language	English
Access Restriction	Open
Subject Keyword	3-chloroperbenzoic acid Acetates Cyclic AMP Cyclic GMP Cyclization Directed acyclic graph Epoxy Resins Ethers Fatty Acids, Unsaturated Fatty Alcohols Hydroxide Ion Methanol Sodium Hydroxide Sugar Alcohols alkyl hydroxyl group organic substance biosynthetic process
Content Type	Text
Resource Type	Article