Synthesis and X-ray crystallographic analysis of chiral pyridyl substituted carbocyclic molecular clefts

Connie K.Y. Lee; Jennifer L. Groneman; Peter Turner; Louis M. Rendina; Margaret M. Harding

doi:10.1016/j.tet.2006.03.014

Synthesis and X-ray crystallographic analysis of chiral pyridyl substituted carbocyclic molecular clefts

Connie K.Y. Lee
, Jennifer L. Groneman
, Peter Turner
, Louis M. Rendina^*
, Margaret M. Harding

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

Ditopic symmetrical bis(pyridyl) ligands incorporating the chiral dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione cleft have been synthesised and characterised by NMR spectroscopy, mass spectrometry and X-ray crystallography. The ligands, which incorporate pyridyl groups directly connected to the carbocyclic cleft core or via alkyne or phenyl linkers were accessed from palladium-catalysed coupling reactions of 2,8-dibromodibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione. X-ray crystal analyses show the interplanar angles between the two cleft aromatic rings in these molecules, which range from 97.80(3) to 109.80(4)°.

Original language	English
Pages (from-to)	4870-4878
Number of pages	9
Journal	Tetrahedron
Volume	62
Issue number	20
DOIs	https://doi.org/10.1016/j.tet.2006.03.014
Publication status	Published - 15 May 2006
Externally published	Yes

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@article{5ab78b9759dd4ee39f1c6bbec479581c,

title = "Synthesis and X-ray crystallographic analysis of chiral pyridyl substituted carbocyclic molecular clefts",

abstract = "Ditopic symmetrical bis(pyridyl) ligands incorporating the chiral dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione cleft have been synthesised and characterised by NMR spectroscopy, mass spectrometry and X-ray crystallography. The ligands, which incorporate pyridyl groups directly connected to the carbocyclic cleft core or via alkyne or phenyl linkers were accessed from palladium-catalysed coupling reactions of 2,8-dibromodibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione. X-ray crystal analyses show the interplanar angles between the two cleft aromatic rings in these molecules, which range from 97.80(3) to 109.80(4)°.",

keywords = "Metal complexation, Molecular clefts, Sonogashira cross-coupling, Supramolecular chemistry, Suzuki cross-coupling, X-ray analysis",

author = "Lee, \{Connie K.Y.\} and Groneman, \{Jennifer L.\} and Peter Turner and Rendina, \{Louis M.\} and Harding, \{Margaret M.\}",

year = "2006",

month = may,

day = "15",

doi = "10.1016/j.tet.2006.03.014",

language = "English",

volume = "62",

pages = "4870--4878",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "20",

}

TY - JOUR

T1 - Synthesis and X-ray crystallographic analysis of chiral pyridyl substituted carbocyclic molecular clefts

AU - Lee, Connie K.Y.

AU - Groneman, Jennifer L.

AU - Turner, Peter

AU - Rendina, Louis M.

AU - Harding, Margaret M.

PY - 2006/5/15

Y1 - 2006/5/15

N2 - Ditopic symmetrical bis(pyridyl) ligands incorporating the chiral dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione cleft have been synthesised and characterised by NMR spectroscopy, mass spectrometry and X-ray crystallography. The ligands, which incorporate pyridyl groups directly connected to the carbocyclic cleft core or via alkyne or phenyl linkers were accessed from palladium-catalysed coupling reactions of 2,8-dibromodibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione. X-ray crystal analyses show the interplanar angles between the two cleft aromatic rings in these molecules, which range from 97.80(3) to 109.80(4)°.

AB - Ditopic symmetrical bis(pyridyl) ligands incorporating the chiral dibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione cleft have been synthesised and characterised by NMR spectroscopy, mass spectrometry and X-ray crystallography. The ligands, which incorporate pyridyl groups directly connected to the carbocyclic cleft core or via alkyne or phenyl linkers were accessed from palladium-catalysed coupling reactions of 2,8-dibromodibenzobicyclo[b,f][3.3.1]nona-5a,6a-diene-6,12-dione. X-ray crystal analyses show the interplanar angles between the two cleft aromatic rings in these molecules, which range from 97.80(3) to 109.80(4)°.

KW - Metal complexation

KW - Molecular clefts

KW - Sonogashira cross-coupling

KW - Supramolecular chemistry

KW - Suzuki cross-coupling

KW - X-ray analysis

UR - https://www.scopus.com/pages/publications/33646022265

U2 - 10.1016/j.tet.2006.03.014

DO - 10.1016/j.tet.2006.03.014

M3 - Article

SN - 0040-4020

VL - 62

SP - 4870

EP - 4878

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

Synthesis and X-ray crystallographic analysis of chiral pyridyl substituted carbocyclic molecular clefts

Abstract

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