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

Fingerprint

Carbohydrates
Ions
Acetic Acid
Bearings (structural)
Benzoic Acid
Molten materials
Carbon
Atoms
Water

Cite this

Buchanan, J. G. ; Conn, J. ; Edgar, A. R. ; Fletcher, R. / The acetolysis and benzolysis of some carbohydrate oxirans. In: Journal of the Chemical Society C: Organic. 1971 ; pp. 1515-1521.
@article{0fbcef6ffd9741e09f34496f74b2c11b,
title = "The acetolysis and benzolysis of some carbohydrate oxirans",
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.",
author = "Buchanan, {J. G.} and J. Conn and Edgar, {A. R.} and R. Fletcher",
year = "1971",
doi = "10.1039/J39710001515",
language = "English",
pages = "1515--1521",
journal = "Journal of the Chemical Society C: Organic",
issn = "0022-4952",
publisher = "Chemical Society",

}

The acetolysis and benzolysis of some carbohydrate oxirans. / Buchanan, J. G.; Conn, J.; Edgar, A. R.; Fletcher, R.

In: Journal of the Chemical Society C: Organic, 1971, p. 1515-1521.

Research output: Contribution to journalArticle

TY - JOUR

T1 - The acetolysis and benzolysis of some carbohydrate oxirans

AU - Buchanan, J. G.

AU - Conn, J.

AU - Edgar, A. R.

AU - Fletcher, R.

PY - 1971

Y1 - 1971

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0343413269&partnerID=8YFLogxK

U2 - 10.1039/J39710001515

DO - 10.1039/J39710001515

M3 - Article

SP - 1515

EP - 1521

JO - Journal of the Chemical Society C: Organic

JF - Journal of the Chemical Society C: Organic

SN - 0022-4952

ER -