Formation of hybrid polymethylene-poly(oxyethylene) macrocycles

S. E. Matthews; C. W. Pouton; M. D. Threadgill

Formation of hybrid polymethylene-poly(oxyethylene) macrocycles

S. E. Matthews, C. W. Pouton, M. 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
Publication status	Published - 2001

Keywords

CROWN-ETHERS

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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author = "Matthews, {S. E.} and Pouton, {C. W.} and Threadgill, {M. D.}",

year = "2001",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

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

AU - Matthews, S. E.

AU - Pouton, C. W.

AU - Threadgill, M. D.

PY - 2001

Y1 - 2001

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

M3 - Article

VL - 42

SP - 1355

EP - 1357

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 7

ER -