Novel ether and thioether macrocycles from phthalaldehyde

R Alan Aitken; Clémence Hauduc; Ross Sinclair McLennan; Alexandra Martha Zoya Slawin; Heather S Wilson

doi:10.1016/j.tetlet.2015.02.003

Novel ether and thioether macrocycles from phthalaldehyde

R Alan Aitken, Clémence Hauduc, Ross Sinclair McLennan, Alexandra Martha Zoya Slawin, Heather S Wilson

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

Abstract

By reaction of phthalaldehyde (benzene-1,2-dicarbaldehyde) with ethane-1,2-diol or 2-mercaptoethanol, macrocycles containing respectively 14- and 12-membered polyether/thioether rings were obtained in low but reproducible yield and their structures confirmed by X-ray diffraction. The simple compounds (2-vinylphenyl)oxirane and 2-oxiranylbenzaldehyde have also been prepared and characterised for the first time.

Original language	English
Pages (from-to)	1937-1940
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	15
Early online date	7 Feb 2015
DOIs	https://doi.org/10.1016/j.tetlet.2015.02.003
Publication status	Published - 8 Apr 2015

Keywords

Macrocycle
Phthalaldehyde
Polyethers
Acetals
X-ray structures

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10.1016/j.tetlet.2015.02.003

TETL-D14-02305
Copyright 2015 Elsevier Ltd. All rights reserved. This is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, 56 (2015) DOI: http://dx.doi.org/10.1016/j.tetlet.2015.02.003
Accepted author manuscript, 644 KB

Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation
Woollins, J. D. (PI), Ashbrook, S. E. (CoI), Morris, R. E. (CoI) & Slawin, A. M. Z. (CoI)
EPSRC
1/01/13 → 31/03/13
Project: Standard

Novel ether and thioether macrocycles from phthalaldehyde (dataset)
Aitken, R. A. (Creator), Hauduc, C. (Creator), McLennan, R. S. (Creator), Slawin, A. M. Z. (Creator) & Wilson, H. S. (Creator), Cambridge Crystallographic Data Centre, 2015
https://dx.doi.org/10.5517/cc13f32q and 2 more links, https://dx.doi.org/10.5517/cc13f34s, https://dx.doi.org/10.5517/cc13f33r (show fewer)
Dataset

Cite this

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title = "Novel ether and thioether macrocycles from phthalaldehyde",

abstract = "By reaction of phthalaldehyde (benzene-1,2-dicarbaldehyde) with ethane-1,2-diol or 2-mercaptoethanol, macrocycles containing respectively 14- and 12-membered polyether/thioether rings were obtained in low but reproducible yield and their structures confirmed by X-ray diffraction. The simple compounds (2-vinylphenyl)oxirane and 2-oxiranylbenzaldehyde have also been prepared and characterised for the first time.",

keywords = "Macrocycle, Phthalaldehyde, Polyethers, Acetals, X-ray structures",

author = "Aitken, {R Alan} and Cl{\'e}mence Hauduc and McLennan, {Ross Sinclair} and Slawin, {Alexandra Martha Zoya} and Wilson, {Heather S}",

year = "2015",

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doi = "10.1016/j.tetlet.2015.02.003",

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T1 - Novel ether and thioether macrocycles from phthalaldehyde

AU - Aitken, R Alan

AU - Hauduc, Clémence

AU - McLennan, Ross Sinclair

AU - Slawin, Alexandra Martha Zoya

AU - Wilson, Heather S

PY - 2015/4/8

Y1 - 2015/4/8

N2 - By reaction of phthalaldehyde (benzene-1,2-dicarbaldehyde) with ethane-1,2-diol or 2-mercaptoethanol, macrocycles containing respectively 14- and 12-membered polyether/thioether rings were obtained in low but reproducible yield and their structures confirmed by X-ray diffraction. The simple compounds (2-vinylphenyl)oxirane and 2-oxiranylbenzaldehyde have also been prepared and characterised for the first time.

AB - By reaction of phthalaldehyde (benzene-1,2-dicarbaldehyde) with ethane-1,2-diol or 2-mercaptoethanol, macrocycles containing respectively 14- and 12-membered polyether/thioether rings were obtained in low but reproducible yield and their structures confirmed by X-ray diffraction. The simple compounds (2-vinylphenyl)oxirane and 2-oxiranylbenzaldehyde have also been prepared and characterised for the first time.

KW - Macrocycle

KW - Phthalaldehyde

KW - Polyethers

KW - Acetals

KW - X-ray structures

U2 - 10.1016/j.tetlet.2015.02.003

DO - 10.1016/j.tetlet.2015.02.003

M3 - Article

SN - 0040-4039

VL - 56

SP - 1937

EP - 1940

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Novel ether and thioether macrocycles from phthalaldehyde

Abstract

Keywords

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Projects

Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

Datasets

Novel ether and thioether macrocycles from phthalaldehyde (dataset)

Cite this