The acetolysis and benzolysis of some carbohydrate oxirans

J. G. Buchanan, J. Conn, A. R. Edgar, R. Fletcher

Research output: Contribution to journalArticle

Abstract

A cyclic acyloxonium ion is formed as an intermediate when a carbohydrate oxiran bearing a vicinal trans-acyloxy-group is heated in acetic acid. In the presence of water the cyclic ion yields a cis-monoester. Under anhydrous conditions, using acetic acid or molten benzoic acid as solvent, three products are generally formed, corresponding to nucleophilic attack at each of the three carbon atoms of the cyclic ion. Possible mechanisms are discussed in the light of other published work on the properties of acyloxonium ions derived from polyols.

Original languageEnglish
Pages (from-to)1515-1521
Number of pages7
JournalJournal of the Chemical Society C: Organic
DOIs
Publication statusPublished - 1971

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