Formation of hybrid polymethylene-poly(oxyethylene) macrocycles

Susan E. Matthews; Colin W. Pouton; Michael D. Threadgill

doi:10.1016/S0040-4039(00)02231-0

Formation of hybrid polymethylene-poly(oxyethylene) macrocycles

Susan E. Matthews, Colin W. Pouton, Michael D. Threadgill

School of Pharmacy

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

1 Citation (Scopus)

Abstract

Maclocyclisations, particularly those forming crown ethers, normally require high dilution conditions. However, treatment of 1,9-bis(sarcosylamino)nonane with alpha,omega -bis(oxiranylmethyl) ethers derived from oligomeric poly(ethyleneglycol)s of MW 400-600 Da under high concentration conditions was found to give excellent yields of 1:1 hybrid polymethylene-poly(oxyethylene) macrocyclic crown ether derivatives. The corresponding alpha,omega -bis(oxiranylmethyl) ether derived from poly(ethyleneglycol) of mean MW 1500 Da gave polymeric material only. The macrocycles were characterised by NMR, GPC and MS. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	1355-1357
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	7
DOIs	https://doi.org/10.1016/S0040-4039(00)02231-0
Publication status	Published - 12 Feb 2001

Keywords

CROWN-ETHERS

Access to Document

10.1016/S0040-4039(00)02231-0

Cite this

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title = "Formation of hybrid polymethylene-poly(oxyethylene) macrocycles",

abstract = "Maclocyclisations, particularly those forming crown ethers, normally require high dilution conditions. However, treatment of 1,9-bis(sarcosylamino)nonane with alpha,omega -bis(oxiranylmethyl) ethers derived from oligomeric poly(ethyleneglycol)s of MW 400-600 Da under high concentration conditions was found to give excellent yields of 1:1 hybrid polymethylene-poly(oxyethylene) macrocyclic crown ether derivatives. The corresponding alpha,omega -bis(oxiranylmethyl) ether derived from poly(ethyleneglycol) of mean MW 1500 Da gave polymeric material only. The macrocycles were characterised by NMR, GPC and MS. (C) 2001 Elsevier Science Ltd. All rights reserved.",

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year = "2001",

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journal = "Tetrahedron Letters",

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T1 - Formation of hybrid polymethylene-poly(oxyethylene) macrocycles

AU - Matthews, Susan E.

AU - Pouton, Colin W.

AU - Threadgill, Michael D.

PY - 2001/2/12

Y1 - 2001/2/12

N2 - Maclocyclisations, particularly those forming crown ethers, normally require high dilution conditions. However, treatment of 1,9-bis(sarcosylamino)nonane with alpha,omega -bis(oxiranylmethyl) ethers derived from oligomeric poly(ethyleneglycol)s of MW 400-600 Da under high concentration conditions was found to give excellent yields of 1:1 hybrid polymethylene-poly(oxyethylene) macrocyclic crown ether derivatives. The corresponding alpha,omega -bis(oxiranylmethyl) ether derived from poly(ethyleneglycol) of mean MW 1500 Da gave polymeric material only. The macrocycles were characterised by NMR, GPC and MS. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - Maclocyclisations, particularly those forming crown ethers, normally require high dilution conditions. However, treatment of 1,9-bis(sarcosylamino)nonane with alpha,omega -bis(oxiranylmethyl) ethers derived from oligomeric poly(ethyleneglycol)s of MW 400-600 Da under high concentration conditions was found to give excellent yields of 1:1 hybrid polymethylene-poly(oxyethylene) macrocyclic crown ether derivatives. The corresponding alpha,omega -bis(oxiranylmethyl) ether derived from poly(ethyleneglycol) of mean MW 1500 Da gave polymeric material only. The macrocycles were characterised by NMR, GPC and MS. (C) 2001 Elsevier Science Ltd. All rights reserved.

KW - CROWN-ETHERS

U2 - 10.1016/S0040-4039(00)02231-0

DO - 10.1016/S0040-4039(00)02231-0

M3 - Article

VL - 42

SP - 1355

EP - 1357

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 7

ER -