Organic compounds of selenium and tellurium

Migalina, Yu. V.; Станинец, В. И.; Lendel, V. G.; Balog, I. M.; Palyulin, Vladimir A.; Koz’min, A. S.; Зефиров, Н. С.

doi:10.1007/bf00479868

Cited by 10 publications

(4 citation statements)

References 4 publications

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“…The 1 H NMR spectra of compounds 5 and 6 showed proton signals for the OCH 2 and CH 2 Br groups as doublets at 5.2-5.4 and 4.1-4.3 ppm in good agreement with literature data [2]. The 1 H NMR spectra of compounds 7 and 8 showed doublet signals at 7.05-7.13 corresponding to the =CHX protons and multiplet signals for the OCH 2 protons at 5.36-5.60 ppm.…”

supporting

confidence: 84%

Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes

Onysko

Lendel

2007

Chem Heterocycl Comp

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There are literature reports of the haloheterocyclization reactions of unsaturated quinoline ethers and thioethers [1] to give heterocyclic systems with oxa(thia)zolinium rings. In continuation of these studies we have selected the 2-allyl(propargyl)oxyquinoline-3-carbaldehydes 3, 4 as model compounds for this haloheterocyclization. These substrates were prepared by conversion of 2-chloro-3-formylquinolines 1 to the corresponding quinolones 2 by treatment with hydrochloric acid and subsequent alkylation using allyl(propargyl) bromides. N R O Cl H 2 O, HCl N R O OH N H R O O N R O O X 2 R O N O X N R O O X 2 R O N O X X X 1a,b 2a,b + 3a,b 5, 6a,b + 4a,b 7, 8a,b KOH KOH CH 2 =CHCH 2 Br HC CCH 2 Br 1 2 3 4 5 6 7 8 -2n+1 -2n+1 1-8 a R = H, b R = Me; 5, 7 Х = Br, n = 0; 6, 8 X = I , n = 1

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supporting

confidence: 84%

Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes

Onysko

Lendel

2007

Chem Heterocycl Comp

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“…A method was developed for the heterocyclization of olefins and acetylenes by the action of selenium and tellurium tetrahalides under phase-transfer conditions (water-diethyl ether), which made it possible to increase the yields of the heterocyclic compounds [148,151,152].…”

Section: Syntheses Of Heterocyclic Compounds By Electrophilic Intramomentioning

confidence: 99%

Chemistry of heterocyclic compounds at the Institute of Organic Chemistry, National Academy of Sciences of Ukraine (Review)

Lozinskii

Il'chenko

2009

Chem Heterocycl Comp

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“…However, with some allylic systems different products and regioselectivities were observed. TeCl 4 adds in an anti-Markovnikov fashion to both CC bonds of Y(CH 2 CHCH 2 ) 2 (Y = O, S, NH, NMe), forming six-membered heterocyclic compounds with two chloromethylene groups at the 2- and 6-positions. , Reaction of diallyamides with TeCl 4 afforded zwitterionic oxazolines, while a rearrangement with a 3→2-shift of the acetyl group was postulated for the reactions of TeCl 4 with allyl esters , We report here the synthesis of the TeCl 4 allyl alcohol adduct and investigations of its molecular structure and that of the TeCl 4 allyl acetate adduct in the solid state and in solution by experimental methods, as well as structural and thermochemical studies for the isolated molecules by ab initio quantum chemical methods.…”

Section: Introductionmentioning

confidence: 99%

Adducts of Tellurium Tetrachloride with Allyl Alcohol and Allyl Acetate: 1,2- vs 1,3-Addition and Structure and Dynamics of Te···O Interactions in Different Phases

2002

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The compounds Cl3Te[CH2CH(Cl)CH2O(H)···]·Cl2Te[−CH2CH(Cl)CH2O−] (1) and Cl3Te[CH2CH(CH2Cl)OC(CH3)O···] (2) were prepared by the reaction of TeCl4 with allyl alcohol and allyl acetate, respectively. Their molecular and crystal structures were investigated by single-crystal X-ray analysis, 1H−1H-NOESY experiments, IR spectroscopy, and ab initio geometry optimization. 1 is a composite compound, whose subunits Cl2Te[−CH2CH(Cl)CH2O−] (1A) and Cl3Te[CH2CH(Cl)CH2O(H)···] (1B) are linked in the solid state via Te···Cl−Te and O···H−O bridges. Both Te atoms are involved in similar five-membered rings, having a covalent Te−O bond in one case (1A) and a dative Te···O bond in the other (1B). In the solid state, both Te atoms are pentacoordinate with pseudo-octahedral configurations. Formation of 2 is accompanied by a 3,2-migration of the acetate group, leading to a 1,3-addition of TeCl4 to allyl acetate and a six-membered ring via an intramolecular dative Te···O interaction. In the solid state, single molecules of 2 are linked by weak CH2Cl···Te contacts, the Te atom being hexacoordinate with a distorted-octahedral configuration. Since reaction of 1 with acetyl chloride also gives 2, the 1,3-addition product of TeCl4 with allyl acetate must be thermodynamically more stable than the corresponding 1,2-addition product, a conclusion that is supported by ab initio calculations. Ab initio calculations (MP2/LANL2DZP) for Cl3Te[CH2CH(Cl)CH2O(H)···] (1B) and 2 revealed strong n(O)−σ*(Te−Cl) and Coulombic interactions for the Te···O bonds, which are significantly longer in the isolated molecules than in the solid state. Multinuclear NMR spectroscopy and 1H−1H-NOESY experiments show the cyclic structures to exist in solution as well, with little changes in their geometry compared to the solid state.

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Organic compounds of selenium and tellurium

Cited by 10 publications

References 4 publications

Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes

Haloheterocyclization of 2-allyl(propargyl)oxyquinoline-3-carbaldehydes

Chemistry of heterocyclic compounds at the Institute of Organic Chemistry, National Academy of Sciences of Ukraine (Review)

Adducts of Tellurium Tetrachloride with Allyl Alcohol and Allyl Acetate: 1,2- vs 1,3-Addition and Structure and Dynamics of Te···O Interactions in Different Phases

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