Synthesis and Structure of Bis‐crown‐Containing Stilbenes (I).

Ведерников, А. И.; Basok, S. S.; Громов, С. П.; Кузьмина, Л. Г.; Avakyan, V. G.; Лобова, Н. А.; Kulygina, E. Yu.; Titkov, T. V.; Strelenko, Yu. À.; Иванов, Э. И.

doi:10.1002/chin.200603166

Cited by 2 publications

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“…Previously, 10 we found that (E)-1a-c and (E)-3,4,3 0 ,4 0tetramethoxystilbene can exist in the crystals as symmetric s-syn,s-syn and s-anti,s-anti conformers differing in the arrangement of the ethylene bond relative to the crown-ether moiety. In solutions, these conformers occur in fast equilibrium in which the former predominates.…”

Section: Resultsmentioning

confidence: 88%

“…For both metallocomplexes 1bÁ(M m+ ) 2 , the s-syn,s-syn conformation of stilbene molecule is found, whereas the s-anti,s-anti conformation was revealed for the crystalline free (E)-1b. 10 The sodium and calcium cations are coordinated by all heteroatoms of the 15-membered macrocycles. Their displacements from the mean plane through the heteroatoms of the nearest macrocycle is only 0.60, 0.68 A ˚for two independent Na(1), Na(2) ions and 1.14 A ˚for the Ca(1) ion, i.e., the metal cations are rather deeply immersed into the macroheterocycle cavities of stilbene 1b.…”

Section: X-ray Diffraction Studies Of Complexes Of Stilbenes (E)-1bcmentioning

confidence: 99%

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Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition

et al. 2011

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It was shown by 1 H NMR spectroscopy that symmetrical bis(crown)stilbenes (L) and small alkali and alkaline-earth metal cations form 1(L) : 1(M m+ ) and 1(L) : 2(M m+ ) complexes in MeCN solutions. In the case of large or hydrated metal cations such as Cs + , Rb + , K + , Ba 2+ , Sr 2+ , [Ca(H 2 O) x ] 2+ and stilbenes with a small crown-ether cavity as compared with the metal cation size, stable bis-sandwich complexes 2(L) : 2(M m+ ) can also be formed. A stable bis-pseudosandwich 2 : 2 complex is also produced from bis(18-crown-6)stilbene with the propanediammonium ion. The effect of the crown-ether size and the cation size and nature on the route of stilbene phototransformation and product composition was elucidated. The bis-(pseudo)sandwich complexes undergo effective stereoselective [2+2] photocycloaddition giving mainly rctt isomers of new 1,2,3,4-tetracrown cyclobutanes. The structures of complexes of bis(crown)stilbenes and obtained cyclobutanes were confirmed by X-ray diffraction.

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Section: Resultsmentioning

confidence: 88%

Section: X-ray Diffraction Studies Of Complexes Of Stilbenes (E)-1bcmentioning

confidence: 99%

Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition

et al. 2011

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“…This disorder, as well as high mosaicity of the crystals, resulted in a decrease in the accuracy of the X ray diffraction data for 3a,c. In spite of this, a comparison of molecules 3a,c,d a In benzene-AcOEt, 10 : 1 (3a-c), benzene-AcOEt, 1 : 1 (3d), benzene-AcOEt, 5 : 1 (3e), benzene-EtOH, 5 : 1 (7-9), and benzene-EtOH, 10 based on the main geometric parameters revealed their common features.…”

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Synthesis of nitro and amino derivatives of benzothiacrown ethers

et al. 2007

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The condensation reaction of 1,2 bis(2 haloethoxy) 4 nitrobenzenes with acyclic α,ω (oxa)alkanedithiols in the presence of alkali metal carbonates produced a series of nitrobenzodithiacrown ethers with macrocycles of different size. The structures of three ethers were established by X ray diffraction. A new method was developed for the synthesis of nitrobenzomonothia 15 crown 5 ether. Nitro derivatives of benzodithiacrown ethers were tested as reagents for extraction of palladium(II), platinum(IV), and rhodium(III) from hydro chloric acid solutions. Extraction of Pd II salts was found to be highly selective compared to that of Pt IV and Rh III salts. Benzodithia 15 crown 5 ether is the most efficient extractant for palladium(II). Reduction of nitrobenzothiacrown ethers with hydrazine hydrate in the pres ence of a platinum catalyst afforded their amino derivatives.Thiacrown ethers are among the most promis ing macrocyclic sulfides. 1,2 Sulfur containing macro heterocycles have attracted interest because these com pounds can form stable complexes with transition and heavy metal ions. 3,4 These compounds can be used as selective extractants, materials for ion selective electrodes, reagents for modifications of chromato graphic sorbents, etc. The development of procedures for the synthesis of important functionalized derivatives of thiacrown ethers is of great importance for the exten sion of the possibilities of the practical use of these com pounds.In the present study, we developed convenient proce dures for the synthesis of nitro and amino derivatives of benzothiacrown ethers with macrocycles of different size and different combinations of O and S atoms. The con densation reactions of 1,2 bis(2 haloethoxy) 4 nitroben zenes 1a,b with terminal (oxa)alkanedithiols 2a-d in the presence of alkali metal carbonates (M 2 CO 3 ) in aqueous ethanol produced nitrobenzodithiacrown ethers 3a-d in 48-89% yields (Scheme 1). To suppress side reactions, Scheme 1

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Synthesis and Structure of Bis‐crown‐Containing Stilbenes (I).

Abstract: Synthesis and Structure of Bis-crown-Containing Stilbenes (I). -(VEDERNIKOV, A. I.; BASOK, S. S.; GROMOV, S. P.; KUZ'MINA, L. G.; AVAKYAN, V. G.; LOBOVA, N. A.; KULYGINA, E. Y.; TITKOV, T. V.; STRELENKO, Y. A.; IVANOV, E. I.; et al.; Russ.

Cited by 2 publications

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Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition

Controlled self-assembly of bis(crown)stilbenes into unusual bis-sandwich complexes: structure and stereoselective [2+2] photocycloaddition

Synthesis of nitro and amino derivatives of benzothiacrown ethers

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