Effect of β-cyclodextrin on the extraction of isoxazolines from aqueous ethanol into chloroform

Christopher J. Easton; C. Merrîcc Hughes; Stephen F. Lincoln; Gregory W. Simpson; George J. Vuckovic

Effect of β-cyclodextrin on the extraction of isoxazolines from aqueous ethanol into chloroform

Christopher J. Easton^*, C. Merrîcc Hughes, Stephen F. Lincoln, Gregory W. Simpson, George J. Vuckovic

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

Regioisomeric pairs of isoxazolines were prepared through reaction of nitrile oxides with ethyl trans-cinnamate. The effect of β -cyclodextrin on the solubility of these compounds in aqueous ethanol and their extraction into chloroform has been examined. Somewhat anomalously, the compound which is least soluble in the aqueous ethanol is least efficiently extracted into the chloroform, presumably because it is most extensively complexed by the cyclodextrin. In one case, extraction of a 1:1 mixture of a regioisomeric pair of isoxazolines resulted in the separation of ca. 50% of each of the compounds in ca. 90% purity, from a single partitioning.

Original language	English
Pages (from-to)	35-43
Number of pages	9
Journal	Arkivoc
Volume	2001
Issue number	12
Publication status	Published - 2001

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title = "Effect of β-cyclodextrin on the extraction of isoxazolines from aqueous ethanol into chloroform",

abstract = "Regioisomeric pairs of isoxazolines were prepared through reaction of nitrile oxides with ethyl trans-cinnamate. The effect of β -cyclodextrin on the solubility of these compounds in aqueous ethanol and their extraction into chloroform has been examined. Somewhat anomalously, the compound which is least soluble in the aqueous ethanol is least efficiently extracted into the chloroform, presumably because it is most extensively complexed by the cyclodextrin. In one case, extraction of a 1:1 mixture of a regioisomeric pair of isoxazolines resulted in the separation of ca. 50% of each of the compounds in ca. 90% purity, from a single partitioning.",

keywords = "Ethyl trans-cinnmate, Extraction, Isoxazolines, Nitrile oxides, β-cyclodextrin",

author = "Easton, {Christopher J.} and Hughes, {C. Merr{\^i}cc} and Lincoln, {Stephen F.} and Simpson, {Gregory W.} and Vuckovic, {George J.}",

year = "2001",

language = "English",

volume = "2001",

pages = "35--43",

journal = "Arkivoc",

issn = "1551-7004",

publisher = "Arkat USA",

number = "12",

}

TY - JOUR

T1 - Effect of β-cyclodextrin on the extraction of isoxazolines from aqueous ethanol into chloroform

AU - Easton, Christopher J.

AU - Hughes, C. Merrîcc

AU - Lincoln, Stephen F.

AU - Simpson, Gregory W.

AU - Vuckovic, George J.

PY - 2001

Y1 - 2001

N2 - Regioisomeric pairs of isoxazolines were prepared through reaction of nitrile oxides with ethyl trans-cinnamate. The effect of β -cyclodextrin on the solubility of these compounds in aqueous ethanol and their extraction into chloroform has been examined. Somewhat anomalously, the compound which is least soluble in the aqueous ethanol is least efficiently extracted into the chloroform, presumably because it is most extensively complexed by the cyclodextrin. In one case, extraction of a 1:1 mixture of a regioisomeric pair of isoxazolines resulted in the separation of ca. 50% of each of the compounds in ca. 90% purity, from a single partitioning.

AB - Regioisomeric pairs of isoxazolines were prepared through reaction of nitrile oxides with ethyl trans-cinnamate. The effect of β -cyclodextrin on the solubility of these compounds in aqueous ethanol and their extraction into chloroform has been examined. Somewhat anomalously, the compound which is least soluble in the aqueous ethanol is least efficiently extracted into the chloroform, presumably because it is most extensively complexed by the cyclodextrin. In one case, extraction of a 1:1 mixture of a regioisomeric pair of isoxazolines resulted in the separation of ca. 50% of each of the compounds in ca. 90% purity, from a single partitioning.

KW - Ethyl trans-cinnmate

KW - Extraction

KW - Isoxazolines

KW - Nitrile oxides

KW - β-cyclodextrin

UR - http://www.scopus.com/inward/record.url?scp=3242739503&partnerID=8YFLogxK

M3 - Article

SN - 1551-7004

VL - 2001

SP - 35

EP - 43

JO - Arkivoc

JF - Arkivoc

IS - 12

ER -

Effect of β-cyclodextrin on the extraction of isoxazolines from aqueous ethanol into chloroform

Abstract

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