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Acid-catalysed isomerisation of epoxides to allylic alcohols

✍ Scribed by A. van Zon; R. Huis

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
438 KB
Volume
100
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The acid‐catalysed isomerisation of epoxides containing tertiary ring carbon atoms results in the selective formation of the corresponding allylic alcohols if the reaction is carried out in methylene chloride or chloroform in the presence of small quantities of sulfuric acid (< 10 mmol/l) or methanesulfonic acid (< 100 mmol/l). The zero‐order kinetics of the isomerisation have been rationalised by a mechanism in which a rapidly and quantitatively formed epoxide‐acid intermediate slowly decomposes into allylic alcohol and acid.

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