sym-[5.5.5]Heterocyclophanes

Structurally well-defined, mixed π/heteroatom-donor macrobicyclic cages

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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
StatePublished - Oct 1998
Externally publishedYes

Fingerprint

Metals
Complexation
Silver
Metal ions
Copper
Crystal structure
Ligands
Electrons

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

sym-[5.5.5]Heterocyclophanes : Structurally well-defined, mixed π/heteroatom-donor macrobicyclic cages. / Hansen, Jens; Blake, Alexander J.; Li, Wan Sheung; Mascal, Mark.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 20, 10.1998, p. 3371-3376.

Research output: Contribution to journalArticle

Hansen, Jens ; Blake, Alexander J. ; Li, Wan Sheung ; Mascal, Mark. / sym-[5.5.5]Heterocyclophanes : Structurally well-defined, mixed π/heteroatom-donor macrobicyclic cages. In: Journal of the Chemical Society - Perkin Transactions 1. 1998 ; No. 20. pp. 3371-3376.
@article{556c5dfee3804b3d93f737fed9b4e687,
title = "sym-[5.5.5]Heterocyclophanes: Structurally well-defined, mixed π/heteroatom-donor macrobicyclic cages",
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.",
author = "Jens Hansen and Blake, {Alexander J.} and Li, {Wan Sheung} and Mark Mascal",
year = "1998",
month = "10",
language = "English (US)",
pages = "3371--3376",
journal = "Journal of the Chemical Society. Perkin Transactions 1",
issn = "1470-4358",
publisher = "Chemical Society",
number = "20",

}

TY - JOUR

T1 - sym-[5.5.5]Heterocyclophanes

T2 - Structurally well-defined, mixed π/heteroatom-donor macrobicyclic cages

AU - Hansen, Jens

AU - Blake, Alexander J.

AU - Li, Wan Sheung

AU - Mascal, Mark

PY - 1998/10

Y1 - 1998/10

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=33748491061&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748491061&partnerID=8YFLogxK

M3 - Article

SP - 3371

EP - 3376

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

SN - 1470-4358

IS - 20

ER -