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Title: Improved synthesis of symmetrically & asymmetrically N -substituted pyridinophane derivatives

Journal Article · · Organic and Biomolecular Chemistry
DOI:https://doi.org/10.1039/c7ob02508d· OSTI ID:1539951
 [1];  [1];  [1];  [1]; ORCiD logo [1]
  1. Department of Chemistry; Washington University; St. Louis; USA
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Reported herein is an optimized, larger-scale synthesis of symmetric and asymmetric pyridinophane tetraazamacrocycles, which are versatile ligands in coordination chemistry.

Research Organization:
Washington Univ., St. Louis, MO (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0006862
OSTI ID:
1539951
Journal Information:
Organic and Biomolecular Chemistry, Vol. 15, Issue 46; ISSN 1477-0520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English

References (46)

Synthesis and Characterisation of the Sodium and Lithium Cryptates of Macrobicyclic Ligands incorporating pyridine, bipyridine, and biisoquinoline units journal August 1988
Reaction of tosylamide monosodium salt with bis(halomethyl) compounds: an easy entry to symmetrical N-tosyl aza macrocycles journal July 1988
718. Attempts to prepare new aromatic systems. Part VII. 15 : 16-Dihydro-15 : 16-diazapyrene. The synthesis of di(pyridine-2 : 6-dimethylene) journal January 1958
Host-guest complexation. 3. Organization of pyridyl binding sites journal September 1977
A simple synthetic route to N,N′-dialkyl-2,11-diaza[3.3](2,6)-pyridinophanes. Crystal structures of N,N′-di-tert-butyl-2,11-diaza[3.3](2,6)pyridinophane and its copper(II) complex journal January 1994
Neutral and Cationic Palladium(II) Complexes of a Diazapyridinophane. Structure, Fluxionality, and Reactivity toward Ethylene journal November 2001
Synthesis and X-ray structure of a monoprotonated salt and of three transition-metal complexes of N,N′-ditertiobutyl-2,11-diaza[3.3](2,6)pyridinophane journal September 2001
Crystal and molecular structure of (N,N'-dimethyl-2,11-diaza[3.3](2,6)pyridinophane)copper dichloride monohydrate complex journal April 1989
Synthesis, Structures, and Spectroscopic Characterization of a Series of N , N ‘-Dimethyl-2,11-diaza[3.3](2,6)pyridinophane Vanadium(III), -(IV), and -(V) Complexes journal January 1996
Evidence for an Unusual Thermally Induced Low-Spin (S=1/2) ⇄ Intermediate-Spin (S=3/2) Transition in a Six-Coordinate Iron(III) Complex: Structure and Electronic Properties of a (1,2-Benzenedithiolato)iron(III) Complex ContainingN,N′-Dimethyl-2,11-diaza[3.3](2,6)pyridinophane as Ligand journal April 1998
A Highly Reactive and Catalytically Active Model System for Intradiol-Cleaving Catechol Dioxygenases: Structure and Reactivity of Iron(III) Catecholate Complexes ofN,N′-Dimethyl-2,11-diaza[3.3](2,6)pyridinophane journal January 1996
Eight-Coordinate Iron(II) and Iron(III) Ions in Complexes with Distorted Dodecahedral FeN8 Environments: Synthesis and Structures of Bis(2,11-diaza[3.3](2,6)pyridinophane)iron Complexes journal March 1996
Synthesis, Crystal Structure, and Potentiometry of Pyridine-Containing Tetraaza Macrocyclic Ligands with Acetate Pendant Arms journal April 1995
Relaxometry, Luminescence Measurement, Electrophoresis, and Animal Biodistribution of Lanthanide(III) Complexes of Some Polyaza Macrocyclic Acetates Containing Pyridine journal April 1995
Synthesis and alkali metal picrate extraction capabilities of novel, cage-functionalized, pyridine containing crown ethers and cryptands journal August 1999
DNA cleavage promoted by Cu2+ complex of cyclen containing pyridine subunit journal March 2007
Biomimetic Catalysis of Catechol Cleavage by O2 in Organic Solvents − Role of Accessibility of O2 to FeIII in 2,11-Diaza[3,3](2,6)pyridinophane-Type Catalysts journal September 2001
Synthesis and X-ray Structure of the Mn II Cl 2 and Mn III F 2 Complexes of N,N ‘ -Dimethyl-2,11-diaza[3,3](2,6)pyridinophane. High-Field Electron Paramagnetic Resonance and Density Funtional Theory Studies of the Mn(III) Complex. Evidence for a Low-Lying Spin Triplet State journal October 2005
Structural and reactivity comparison of analogous organometallic Pd(iii) and Pd(iv) complexes journal January 2012
Structure and electronic properties of Pd(III) complexes journal January 2013
Stable Mononuclear Organometallic Pd(III) Complexes and Their C−C Bond Formation Reactivity journal June 2010
cis -Dihydroxylation of Alkenes with Oxone Catalyzed by Iron Complexes of a Macrocyclic Tetraaza Ligand and Reaction Mechanism by ESI-MS Spectrometry and DFT Calculations journal September 2010
How Does a Coordinated Radical Ligand Affect the Spin Crossover Properties in an Octahedral Iron(II) Complex? journal May 2014
Temperature-Induced Spin-Transition in a Low-Spin Cobalt(II) Semiquinonate Complex journal December 2009
Late First-Row Transition Metal Complexes of a Tetradentate Pyridinophane Ligand: Electronic Properties and Reactivity Implications journal June 2012
Water oxidation catalysed by iron complex of N,N′-dimethyl-2,11-diaza[3,3](2,6)pyridinophane. Spectroscopy of iron–oxo intermediates and density functional theory calculations journal January 2015
A Robust Mn Catalyst for H 2 O 2 Disproportionation in Aqueous Solution journal May 2013
Ligand Modification Transforms a Catalase Mimic into a Water Oxidation Catalyst journal July 2014
Organometallic Nickel(III) Complexes Relevant to Cross-Coupling and Carbon–Heteroatom Bond Formation Reactions journal April 2014
Isolated Organometallic Nickel(III) and Nickel(IV) Complexes Relevant to Carbon–Carbon Bond Formation Reactions journal September 2016
Steric Effect on the Nucleophilic Reactivity of Nickel(III) Peroxo Complexes journal June 2015
Perturbation of the O–U–O Angle in Uranyl by Coordination to a 12-Membered Macrocycle journal May 2016
Lanthanide Complexes Based on a Diazapyridinophane Platform Containing Picolinate Pendants journal September 2012
Reversible constitutional switching between macrocycles and polymers induced by shape change in a dynamic covalent system journal January 2009
New Approach to Ru(II) Pincer Ligand Chemistry. Bis( t ert -butylaminomethyl)pyridine Coordinated to Ruthenium(II) journal April 2000
Probing the Steric and Electronic Characteristics of a New Bis-Pyrrolide Pincer Ligand journal January 2014
Synthesis and Structures of Novel Pyridine-Bridged Phanes of 4,4′-Bipyridine journal September 1999
Formation of very stable and selective Cu(ii) complexes with a non-macrocyclic ligand: can basicity rival pre-organization? journal January 2010
The Synthesis and Property of Dihydropyrene Derivatives Containing a Nitrogen Atom journal August 2007
Generation of (nonafluoro-tert-butoxy)methyl ponytails for enhanced fluorous partition of aromatics and heterocycles journal January 2012
Synthesis and coordinating properties of ligands designed for modeling of the active site zinc of liver alcohol dehydrogenase journal March 1990
Self-Complementary [2]Catenanes and Their Related [3]Catenanes journal June 2000
Linear and macrocyclic ligands containing alternating pyridine and imidazolidin-2-one units 1 journal January 1998
Facile synthesis of methanesulfonate esters journal September 1970
Steuerung der Bildungsselektivität vielgliedriger Oligomerer durch Templat- und Caesium-Effekt journal August 1983
Isolation of Key Organometallic Aryl-Co(III) Intermediates in Cobalt-Catalyzed C(sp 2 )–H Functionalizations and New Insights into Alkyne Annulation Reaction Mechanisms journal October 2016

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