Reversible-irreversible approach to schiff base macrocycles: Access to isomeric macrocycles with multiple salphen pockets

Peter D. Frischmann, Jian Jiang, Joseph Ka Ho Hui, Joseph J. Grzybowski, Mark J. MacLachlan

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

We have developed methodology for the formation of a new family of metal-free Schiff base macrocycles utilizing the differential exchange rates of aldimines and ketimines. The more robust ketimine bond Is kinetically Inert under the milder conditions used for aldimine bond formation. In particular, this route enables access to the first conjugated macrocycles with four unsymmetrical N2O2 salphen-like pockets.

Original languageEnglish
Pages (from-to)1255-1258
Number of pages4
JournalOrganic Letters
Volume10
Issue number6
DOIs
Publication statusPublished - Mar 20 2008

Fingerprint

Schiff Bases
imines
Metals
routes
methodology
metals
ketimine
salphen

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Reversible-irreversible approach to schiff base macrocycles : Access to isomeric macrocycles with multiple salphen pockets. / Frischmann, Peter D.; Jiang, Jian; Hui, Joseph Ka Ho; Grzybowski, Joseph J.; MacLachlan, Mark J.

In: Organic Letters, Vol. 10, No. 6, 20.03.2008, p. 1255-1258.

Research output: Contribution to journalArticle

Frischmann, Peter D. ; Jiang, Jian ; Hui, Joseph Ka Ho ; Grzybowski, Joseph J. ; MacLachlan, Mark J. / Reversible-irreversible approach to schiff base macrocycles : Access to isomeric macrocycles with multiple salphen pockets. In: Organic Letters. 2008 ; Vol. 10, No. 6. pp. 1255-1258.
@article{9a2fb53520eb4ea0b65b98834f10235f,
title = "Reversible-irreversible approach to schiff base macrocycles: Access to isomeric macrocycles with multiple salphen pockets",
abstract = "We have developed methodology for the formation of a new family of metal-free Schiff base macrocycles utilizing the differential exchange rates of aldimines and ketimines. The more robust ketimine bond Is kinetically Inert under the milder conditions used for aldimine bond formation. In particular, this route enables access to the first conjugated macrocycles with four unsymmetrical N2O2 salphen-like pockets.",
author = "Frischmann, {Peter D.} and Jian Jiang and Hui, {Joseph Ka Ho} and Grzybowski, {Joseph J.} and MacLachlan, {Mark J.}",
year = "2008",
month = "3",
day = "20",
doi = "10.1021/ol8001317",
language = "English",
volume = "10",
pages = "1255--1258",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "6",

}

TY - JOUR

T1 - Reversible-irreversible approach to schiff base macrocycles

T2 - Access to isomeric macrocycles with multiple salphen pockets

AU - Frischmann, Peter D.

AU - Jiang, Jian

AU - Hui, Joseph Ka Ho

AU - Grzybowski, Joseph J.

AU - MacLachlan, Mark J.

PY - 2008/3/20

Y1 - 2008/3/20

N2 - We have developed methodology for the formation of a new family of metal-free Schiff base macrocycles utilizing the differential exchange rates of aldimines and ketimines. The more robust ketimine bond Is kinetically Inert under the milder conditions used for aldimine bond formation. In particular, this route enables access to the first conjugated macrocycles with four unsymmetrical N2O2 salphen-like pockets.

AB - We have developed methodology for the formation of a new family of metal-free Schiff base macrocycles utilizing the differential exchange rates of aldimines and ketimines. The more robust ketimine bond Is kinetically Inert under the milder conditions used for aldimine bond formation. In particular, this route enables access to the first conjugated macrocycles with four unsymmetrical N2O2 salphen-like pockets.

UR - http://www.scopus.com/inward/record.url?scp=53249126809&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=53249126809&partnerID=8YFLogxK

U2 - 10.1021/ol8001317

DO - 10.1021/ol8001317

M3 - Article

C2 - 18288856

AN - SCOPUS:53249126809

VL - 10

SP - 1255

EP - 1258

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 6

ER -