sym-[5.5.5]Heterocyclophanes: Structurally well-defined, mixed π/heteroatom-donor macrobicyclic cages

Jens Hansen, Alexander J. Blake, Wan Sheung Li, Mark Mascal

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Abstract

Structural considerations for achieving conformational stability in cyclophanes are applied as design criteria in the synthesis of sym-[5.5.5]triaza- and sym-[5.5.5]trioxacyclophane macrobicycles. These compounds act as dynamic hosts in which the metal ion migrates between equivalent, C3-related (η1-C)2N2 coordination sites. The metal-arene interaction may alternatively be described as three centre, two-electron σ complexation to the C-H bond. Crystal structures of the copper(I) and silver(I) complexes show that little reorganization is required on the part of the ligand to accommodate the metal, and the former provides an unusual, structurally characterized example of eta-bonding of an arene to Cu1.

Original languageEnglish (US)
Pages (from-to)3371-3376
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number20
Publication statusPublished - Oct 1998
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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