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

Peter D. Frischmann, Jian Jiang, Joseph K.H. Hui, Joseph J. Grzybowski, Mark J. MacLachlan

Research output: Contribution to journalArticlepeer-review

61 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
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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