Structural and complexation properties of 2,11-diselena[3.3](2,6)pyridinophane

Muralidharan, S.; Hojjatie, Massoud; Firestone, Millicent A.; Freiser, Henry

doi:10.1021/jo00263a025

Cited by 35 publications

(10 citation statements)

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“…4). A similar coordination geometry around the metal center was previously reported for N4S2 macrocyclic Ni(II) complexes [34][35][36]. The longer M-Se/M-Te (Table 3) bonds are due to the ''hard'' N and ''soft'' Se/Te bonding.…”

Section: Coordination With Ni Pd and Ptsupporting

confidence: 77%

“…A similar reaction of PtCl 2 and 17 (reduced from 3) gives brick red crystals of 41 (Scheme 12) [32,36]. The structure of 41 …”

Section: Compound Numbersmentioning

confidence: 99%

“…Adaptability of the ligands leads to a cis-disposition of Se/Te donors. Only one other structural example of Ni(II) complex of selenaaza macrocycles has been reported [36], although there is also an example of Table 2 Selected bond lengths (Å) and angles (°) of the Schiff base macrocycles and polyamine derivatives.…”

Section: Coordination With Ni Pd and Ptmentioning

confidence: 99%

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Chemistry of selenium/tellurium-containing Schiff base macrocycles

Panda

Srivastava

et al. 2011

Inorganica Chimica Acta

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Section: Coordination With Ni Pd and Ptsupporting

confidence: 77%

“…A similar reaction of PtCl 2 and 17 (reduced from 3) gives brick red crystals of 41 (Scheme 12) [32,36]. The structure of 41 …”

Section: Compound Numbersmentioning

confidence: 99%

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Chemistry of selenium/tellurium-containing Schiff base macrocycles

Panda

Srivastava

et al. 2011

Inorganica Chimica Acta

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“…[25] The first host molecule containing an Se-Se bond has been synthesized by Tomoda et al [26] Muralidharan et al have described a selenium-containing cyclophane and also studied its complexation. [27] Another novel tetraselenide macrocycle has been synthesized by Furukawa and co-workers. [28] Polyselenoether macrocycles have also been synthesized from 3,3-dimethylselenatane which is cyclooligomerized catalytically at 115°C in the presence of [Re 2 (CO) 9 (SeCH 2 CMe 2 CH 2 )].…”

Section: )]mentioning

confidence: 99%

Synthesis, Characterization and Coordination Chemistry of Some Selenium‐Containing Macrocyclic Schiff Bases

et al. 2005

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“…Among the various types of [3.3]MPyPs, the [3.3](2,6)PyPs have been studied in detail and the 2,11-diaza, 2 dithia, 3 dioxa, 4 and diselena derivatives 5 have been synthesized along with all the carbon parent cyclophanes 6 ( Figure 1). These PyPs have served as ligands for transition-metal complexes, and various kinds of metal complexes have been prepared.…”

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confidence: 99%

Synthesis of Multilayered [3.3](3,5)Pyridinophanes

Shibahara

Watanabe²,

Aso

et al. 2008

Synthesis

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(3,5)pyridinophanes (PyPs) have been synthesized by the (4-tolylsulfonyl)methyl isocyanide (TosMIC) method. The coupling reaction between 3,5-bis[2-isocyano-2-(4-tolylsulfonyl)ethyl]pyridine (TosMIC adduct) and bis(chloromethyl) or tetrakis(bromomethyl) compounds in the presence of sodium hydride in N,N-dimethylformamide or sodium hydroxide and tetrabutylammonium iodide under high-dilution conditions gave the two-layered dione or three-and four-layered tetraones. Wolff-Kishner reduction of the ketones afforded the desired two-to four-layered [3.3](3,5)PyPs. The structure of the dione units take an anti geometry whereas the cyclophane units take a syn geometry in solution.[3.3]Metapyridinophanes (MPyPs) are composed of two pyridine rings and two three-atom bridges connected to them. Among the various types of [3.3]MPyPs, the [3.3](2,6)PyPs have been studied in detail and the 2,11-diaza, 2 dithia, 3 dioxa, 4 and diselena derivatives 5 have been synthesized along with all the carbon parent cyclophanes 6 ( Figure 1). These PyPs have served as ligands for transition-metal complexes, and various kinds of metal complexes have been prepared. 5,7 Their conformational isomerism has also attracted much attention. 8 In contrast, a limited number of [3.3](3,5)PyP are known to date, mainly due to the instability of the coupling precursor, 3,5-bis(halomethyl)pyridine. In our recent preparation of 2,11-diaza[3.3](3,5)PyP, freshly prepared 3,5-bis(chloromethyl)pyridine was used for the coupling reaction. 9 One of the major advantages of the [3.3](3,5)PyPs over the [3.3](2,6)PyPs is the potential ability to form selfassembled supramolecules upon coordination, because the cyclophanes take syn geometry and the nitrogen lone pair electrons can readily coordinate to metals without steric hindrance by the bridges. For example, the formation of the double-decker type 2:2 complexes has been reported in 2,11-diaza-10 and dithia[3.3](3,5)PyPs. 11In previous papers, we reported the synthesis of multilayered [3.3]cyclophanes by the (4-tolylsulfonyl)methyl isocyanide (TosMIC) method (metacyclophanes; MCPs) 12 and (4-ethylphenylsulfonyl)methyl isocyanide (EbsMIC) method (paracyclophanes; PCPs). 13 Therefore, multilayered MCPs incorporating pyridine rings at both ends may form larger supramolecules upon complexation with the transition metals and new types of supramolecules may serve as catalysts, inclusion hosts, and nanometer-scale materials. We now report the synthesis of two-to fourlayered [3.3](3,5)PyPs 1-3 and their structures in solution by 1 H NMR studies. Multilayered [3.3](3,5) PyPs 1-3 were synthesized by theTosMIC method in the critical coupling reaction (Scheme 1). The synthetic key intermediates for the synthesis of multilayered PyPs are bis(chloromethyl)pyridine 4 9 and its TosMIC adduct 6. 3,5-Bis(chloromethyl)pyridine (4) was synthesized by chlorination of 3,5-lutidine with N-chlorosuccinimide in carbon tetrachloride followed by column chromatography on silica gel (n-hexane-EtOAc, 3:1; R f = 0.20) to give 4 in 32% yield. The...

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Structural and complexation properties of 2,11-diselena[3.3](2,6)pyridinophane

Cited by 35 publications

References 0 publications

Chemistry of selenium/tellurium-containing Schiff base macrocycles

Chemistry of selenium/tellurium-containing Schiff base macrocycles

Synthesis, Characterization and Coordination Chemistry of Some Selenium‐Containing Macrocyclic Schiff Bases

Synthesis of Multilayered [3.3](3,5)Pyridinophanes

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