Method of obtaining bis-(endo-bicyclo[4,2,1]none-2,4-dienes)

FIELD: chemistry.

SUBSTANCE: invention relates to method of obtaining bis-(endo-bicyclo[4.2.1]none-2,4-dienes) of general formula (1), n = 0, 1, 2, 4. α,ω-diallenes of general formula interact with 1,3,5-cycloheptatriene (CHT) in presence of catalytic system TiCl4-Et2AlCl, with molar ratio α,ω-diallene:CHT:TiCl4:Et2AlCl = (9-11):20:(0.1-0.3):4, temperature 20-80°C, in benzene, for 10-48 h.

EFFECT: application of claimed invention makes it possible to obtain target compounds.

11 ex, 1 tbl

 

The present invention relates to methods of producing new polycyclic compounds, specifically to a method for producing bis-{endo-bicyclo[4.2.1]Nona-2,4-dienes) of the General formula (1):

This compound belongs to the class of intense energy consuming systems and may find application as components of high-energy fuels for air-breathing missile systems (G. W. Burdette, H. R. Lander, J. R. McCoy, J. Energy. 1978, 2, 289), intermediates in the synthesis of modern medicines exhibiting anticancer, antiviral and other activities (N. A. Petasis, M. A. Patane, Tetrahedron. 1992, 48, 5757).

The known method [J. H. Rigby, S. B. Laurent, Z. Kamal, M. J. Heeg. Chromium(0)-promoted [6π+2π] cycloadditions of allenes with cycloheptatriene // J. Org. Lett, 2008, V. 10, 5609] obtain cycloadduct (2) the photochemical reaction [6π+2π]-cycloaddition (η6-cycloheptatrien)tricarbonylchromium(0) allens:

The known method cannot be obtained bis-(endo-bicyclo[4.2.1]Nona-2,4-dienes) of the General formula (1).

The known method [H. Clavier, K. L. Jeune, I. Riggi, A. Tenaglia, G. Buono. Highly selective cobalt-also been other ideas where [6+2] cycloaddition of cycloheptatriene and allenes // J. Org. Lett, 2011, V. 13, P. 308] obtain cycloadduct (2) reaction [6π+2π]-cycloaddition of 1,2-dienes to 1,3,5-cycloheptatriene (CHT) in the presence of catalytic systems [CoI2, dppe, Zn, zni extension2]:

From�this way cannot be obtained bis-(endo-bicyclo[4.2.1]Nona-2,4-dienes) of the General formula (1).

The known method [V. A. Dyakonov, G. N. Kadikova, U. M. Dzhemilev. Ti-catalyzed [6π+2π] cycloadditions of allenes with 1,3,5-cycloheptatriene // Tetrahedron Letters, 2011, V. 52, P. 2780] obtain cycloadduct (2) reaction [6π+2π]-cycloaddition of 1,2-dienes to CHT in the presence of a catalytic system TiCl4-Et2AlCl at a temperature of 80°C in benzene for 8 hours under the scheme:

The known method cannot be obtained bis-(endo-bicyclo[4.2.1]Nona-2,4-dienes) of the General formula (1).

Thus, in the literature there are no data on the synthesis of bis-(endo-bicyclo[4.2.1]Nona-2,4-dienes) of formula (1).

The method of synthesis of bis-(endo-bicyclo[4.2.1]Nona-2,4-dienes) of the General formula (1).

The method consists in the interaction of α,ω-gillinov of the General formula (3) with CHT in the presence of a catalytic system TiCl4-Et2AlCl, taken in the molar ratio of α,ω-Dillen:CGT:TiCl4:Et2AlCl=(9-11):20:(0.1-0.3):4, preferably 10:20:0.2:4. The reaction is carried out in an ampoule at a temperature of 20-80°C. the reaction Time 10-48 h, the yield of the target product 46-81%. As a solvent it is necessary to use benzene.

The reaction proceeds according to the scheme:

Target products (1) are formed only with the participation of α,ω-gillinov, CGT and catalytic system TiCl4-Et2AlCl. In the presence of other transition metal complexes (for example, Cp2ZrCl2, Cp2 2, Zr(acac)4, Pd(ASAS)2, Ni(ASAS)2, Fe(ASAS)3) target products (1) are not formed.

Conducting the reaction in the presence of a catalyst TiCl4more than 0.3 mmol to 10 mmol of α,ω-dialene does not significantly increase the yield of target products (1). The use in the reaction of the catalyst TiCl4less than 0.1 mmol to 10 mmol of α,ω-dialene reduces the yield of the adduct (1), which is associated with a reduction of catalytically active sites in the reaction mass. The experiments were performed at heating 20-80°C. At a higher temperature (e.g. 120°C) decreases the output of ademero, probably due to side processes of decomposition and polymerization. At a lower temperature (e.g. 20°C) decreases the reaction rate.

The proposed method has the following advantages

1. The method allows to obtain high yields of the individual bis-(endo-bicyclo[4.2.1]Nona-2,4-dienes) (1), the synthesis of which is described in the literature.

The method is illustrated by the following examples

EXAMPLE 1. In constant-temperature (~0°C) glass ampoule in an atmosphere of dry argon was loaded with 2 g (20 mmol) of 1,3,5-cycloheptatriene, 1 g (10 mmol) of DECA-1,2,8,9-tetraene, 0.022 ml (0.2 mmol) of TiCl4in 1 ml of benzene and 3 ml of dry benzene. The ampoule was cooled to liquid nitrogen temperature, was loaded with 0.6 ml (4 mmol, 90.2%) Et2AlCl in 1 ml of benzene and sealed. After napr�tion at 80°C for 10 h, the ampoule was opened, the contents were treated with C2H5OH. Have a 1,6-diligen-bis-(bicyclo[4.2.1]Nona-2,4-dienyl)hexane (1) with a yield of 78%.

The spectral characteristics of the adduct (1):

The NMR spectrum1H (CDCl3d, M. D.) 1,6-diligen-bis-(bicyclo[4.2.1]Nona-2,4-dienyl)hexane (1): 1.18-1.37 (m, 4H, C(12,12')H2); 1.89-1.97 (m, 4H, C(VAG com 11.11')H2); 1.93 (d, 2H, C(9,9')H2, J=12 Hz); 2.23 (dt, 2H, C(9,9')H2, JD=12, JT=7 Hz); 2.47 (DD, 2H, C(8,8')H2, J=16 Hz); 2.58 (d, 2H, C(8,8')H2, J=16 Hz); 2.73-2.78 (m, 2H, C(1,1') (H); 3.26-3.30 (m, 2H, C(6,6') (H); 5.13 (t, 2H, C(10,10'), J=7 Hz); 5.59-5.66 (m, 4H, C(3,3',4,4')H); 5.97-6.05 (m, 4H, C(2,2',5,5')H)

The NMR spectrum13C (CDCl3d, M. D.) 1,6-diligen-bis-(bicyclo[4.2.1]Nona-2,4-dienyl)hexane (1): (E): C 29.07(to 11.11'); 29.27 C(12,12'); 32.18 C(9,9'); at 38.58 C(1,1'); 42.23 C(8,8'); 45.50 C(6,6'); 120.79 C(10,10'); 123.12 (C(4,4'); 123.49 C(3,3'); 138.13 C(5,5'); 138.78 C(2,2'); 151.33 C(7,7'). (Z): C 29.05(TO 11.11'); 29.32 C(12,12'); 32.94 C(9,9'); 39.19 (C(1,1'); 43.13 C(6,6'); 47.30 C(8,8'); 119.05 C(10,10'); 123.38 C(4,4'); 124.33 (C(3,3'); 136.61 C(5,5'); 137.91 C(2,2'); 149.52 C(7,7').

Other examples of the method are shown in table 1.

Method for producing bis-(endo-bicyclo[4.2.1]Nona-2,4-dienes) of the General formula (1):

characterized in that the α,ω-valley of the General formulainteract with 1,3,5-cycloheptatriene (CHT) in the presence of a catalytic system TiCl4-Et2AlCl, with a molar ratio of α,ω-Dillen:TiCl 4:Et2AlCl= (9-11):20:(0.1-0.3):4, a temperature of 20-80°C, in benzene, for 10-48 h.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 2-endo-ethyl-5-exo-ethylpentacyclo[8.4.0.03.7.04.14.06.11]tetradeca-8,12-diene of formula (1) The method is characterised by that homogenisation of 7-ethyl-1,3,5-cycloheptatriene (C9H12) is carried out in the presence of a catalyst system TiX2Cl2-Et2AlCl (X=Cl, acac, i-PrO), with molar ratio C9H12:TiX2Cl2:Et2AlCl = 10:(0.1-0.3):4, in an argo atmosphere at 20-100°C in benzene for 8-48 hours.

EFFECT: method enables to separately obtain the desired compound.

9 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing pentacyclo[7.5.0.02.8.05.14.07.11]tetradeca-3,12-diene of formula The method is characterised by catalytic dimerisation of 1,3,5-cycloheptatriene (CHT). The catalyst system used is NbCl5-Et2AlCl. The reaction is carried out with molar ratio CHT:NbCl5:Et2AlCl=10:(0.1-0.3):4, in argon atmosphere, at 20-100°C, in benzene for 8-48 hours.

EFFECT: method enables to separately obtain the end product.

1 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method for combined production of pentacyclo[7.5.0.02.8.05.14.07.11]tetradeca-3,12-diene of formula

and pentacyclo[8.4.0.03.7.04.14.06.11]tetradeca-8,12-diene of formula

The method includes homogenisation of 1,3,5-cycloheptatriene (CHT) in the presence of a Ti-containing catalyst system, and is characterised by that the catalyst used is Ti(acac)2Cl2-Et2AlCl, the reaction is carried out with molar ratio CHT:Ti(acac)2Cl2:Et2AlCl=10:(0.1-0.3):4, in an argon atmosphere, at 5-80°C, in benzene for 6-72 hours.

EFFECT: method enables to use a more stable catalyst and reduces power consumption.

1 tbl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing pentacyclo[8.4.0.03.7.04.14.06.11]tetradeca-8,12-diene of formula The method is characterised by catalytic dimerisation of 1,3,5-cycloheptatriene (CHT). The catalyst used is Ni(acac)2-Et2AlCl. The reaction is carried out with molar ratio CHT:Ni(acac)2:Et2AlCl=10:(0.1-0.3):4, in an argon atmosphere, at 20-100°C, in benzene for 8-48 hours.

EFFECT: method enables to obtain the end product separately.

7 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing bicyclo[4,2,1]nona-2,4-dienes of general formula where R=H, -(CH2)6-; R1=Me, Bu, Hex, Ph, Bn, -(CH2)6-, -(CH2)5-, CH2TMS, R2=H, -(CH2)5-, Ph, CH2TMS via catalytic reaction of 1,2-dienes with 1,3,5-cycloheptatriene (CHT). The catalyst system used is Ti(acac)2Cl2-Et2AlCl, the 1,2-diene used is a compound of general formula (where R, R1, R2 are described above), the reaction is carried out with molar ratio 1,2-diene:CHT:Ti(acac)2Cl2:Et2AlCl=(10-14):10:(0.1-0.3):4 in an ampoule at 20-80°C, in benzene for 6-48 hours.

EFFECT: invention reduces power consumption and enables to use a more stable catalyst.

17 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: method of hydrocarbon aromatisation includes: a) contacting of alkane containing from 2 to 6 carbon atom in molecule with at least one catalyst consisting virtually of platinum applied to zeolite MFI which lattice consists virtually from gallium, silicon and oxygen and b) separation of aromatic products. The preparation method for platinum-gallium zeolite catalyst used for hydrocarbon aromatisation is described, it includes: preparation of gallium zeolite containing silicon and gallium; precipitation of the platinum to said zeolite; and c) zeolite calcination. In the said method the said gallium zeolite catalyst consists virtually of platinum applied to zeolite MFI which lattice consists virtually from gallium, silicon and oxygen. The platinum- gallium zeolite catalyst for hydrocarbon aromatisation containing: a) gallium-silicon zeolite and b) platinum precipitated to gallium-silicon zeolite is also described. In the said method the said platinum-gallium zeolite catalyst consists virtually of platinum applied to zeolite MFI which lattice consists virtually from gallium, silicon and oxygen.

EFFECT: enhancing of the catalyst selectivity in transforming of lower alkanes to aromatic hydrocarbons.

30 cl, 3 dwg, 4 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention refers to method of reaction of alkene(s) contained in hydrocarbon stream, and in a reaction-rectifying system provided with rectifying sections and in between reaction zones with subnatant catalyst. The fluid is poured from the top of each overlying zone to the bottom of underlying zone. It is followed with partial disperse passing of vapour flow from underlying zone through each reaction zone. Thus residual vapour flow from each underlying zone is backflow to the top of overlying reaction zone through overflow space to poured fluid. As a rule, higher-boiling reagent is nontertiary alcohol, carboxylic acid or benzene, while essential reaction product is ether, ester or alkylbenzene.

EFFECT: improved method.

7 cl, 3 dwg, 6 ex

FIELD: chemistry.

SUBSTANCE: method of 4-vinylcyclohexene production includes stages as follows: (A) preparation of n-butane-containing original gas flow, (B1) delivery of n-butane-containing original gas flow to the first dehydrogenation area and catalytic nonoxidation dehydrogenation of n-butane thus producing for gaseous product stream containing n-butane, 1-butene, 2-butene and as necessary, butadiene and secondary components, (B2) delivery of gaseous product stream containing n-butane, 1-butene, 2-butene, as necessary, butadiene and as necessary, secondary components to the second dehydrogenation area and oxidation dehydrogenation of 1-butene and 2-butene to butadiene thus producing gaseous product stream of s containing butadiene, n-butane, water vapour and as necessary secondary components, (C) delivery of product stream from dehydrogenation stage, if required after water vapour separation and secondary components, to dimerisation area and catalytic dimerisation of butadiene thus producing product stream containing 4-vinylcyclohexene, n-butane and, if required, 1-butene, 2-butene and unreacted butadiene, and (D) separation of 4-vinylcyclohexene from product stream of dimerisation stage and recirculation of n-butane and, if required, 1-butene, 2-butene and unreacted butadiene to dehydrogenation area. Method of ethylbenzol or styrene production includes aforesaid stages (A)-(D) and additional stage (E) delivery of 4-vinylcyclohexene to further dehydrogenation area and catalytic dehydrogenation to ethylbenzol or oxidation dehydrogenation with oxygen added thus making styrene.

EFFECT: method profitability, less by-products.

6 cl, 4 dwg, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a novel compound of general formula I

,

and a pharmaceutically acceptable salt thereof, where X denotes CH2, CHF or S, Y denotes CN, R1, R2, R3 and R4 denotes hydrogen, n equals 1, m equals 0 or 1, R denotes R11, R12 or R13, where R11 includes at least one group selected from the following b) or c), where optionally substituted heterocyclic and heteroaryl groups are bonded with a noradamantyl part either directly or through a methylene adjacent group or a C-C bond or C-N bond; b) the substituted 5-member heteroaryl group, in which the heteroaryl ring is a monocyclic aromatic ring system, includes two or more heteroatoms selected from nitrogen and oxygen; c) the heterocyclic group is optionally substituted with a C1-C3 alkyl or oxo group, where the heterocyclic ring system is a 5-9-member mono- or bicyclic ring system with one or more heteroatoms selected from a group consisting of nitrogen and sulphur, where heteroatoms can also be present as functional groups, where the heterocyclic ring system can contain one or two double bonds, and where the monocyclic heterocyclic ring can be condensed with a phenyl ring, R12 is selected from hydrogen, halogen, hydroxy, amino and C1-C4 alkoxy; R13 is a substituted phenyl, where the substitutes, which can be identical or different, include at least one group selected from a) hydrogen; b) nitro, amino; c) the saturated or unsaturated monocyclic heterocyclic ring system is optionally substituted with one or more groups selected from C1-C3 alkyl and oxo, where the heterocyclic ring system is a 5-member ring with one or more heteroatoms selected from a group consisting of nitrogen and sulphur, where the heteroatoms can also be present as functional groups. The present invention also relates to a pharmaceutical composition having dipeptidyl peptidase IV inhibiting activity, methods of obtaining the novel compound of formula I and use in treating type II diabetes and diabetic complications as well as for treating dyslipidaemia, hypercholesteremia, obesity and hyperglycaemia.

EFFECT: novel dipeptidyl peptidase IV inhibitors.

10 cl, 1 tbl, 43 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing bicyclo[4,2,1]nona-2,4-dienes of general formula where R=H, -(CH2)6-; R1=Me, Bu, Hex, Ph, Bn, -(CH2)6-, -(CH2)5-, CH2TMS, R2=H, -(CH2)5-, Ph, CH2TMS via catalytic reaction of 1,2-dienes with 1,3,5-cycloheptatriene (CHT). The catalyst system used is Ti(acac)2Cl2-Et2AlCl, the 1,2-diene used is a compound of general formula (where R, R1, R2 are described above), the reaction is carried out with molar ratio 1,2-diene:CHT:Ti(acac)2Cl2:Et2AlCl=(10-14):10:(0.1-0.3):4 in an ampoule at 20-80°C, in benzene for 6-48 hours.

EFFECT: invention reduces power consumption and enables to use a more stable catalyst.

17 ex, 1 tbl

FIELD: chemistry.

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EFFECT: increased output.

1 tbl, 10 ex

FIELD: chemistry.

SUBSTANCE: disclosed is a method of producing Si-containing bis-(endo-bicyclo[4.2.1]none-2,4,7-trienes) by reacting Si-containing acetylenes with 7,7'-dypropilbutane in the presence of a Ti(acac)2Cl2-Et2AlCl catalyst system at 20-80°C in benzene for 12-48 hours.

EFFECT: method provides high output of said compositions, which can be used as components of high-energy fuels for air-jet-rocket systems and intermediate products in synthesis of modern medical drugs.

1 tbl, 9 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: tetra-(meso-aryl)porphyrin with diisobornylphenol substitutes of formula I , wherein the isobornyl fragments are configured as chiral centres (1S,2R,4R,1'R,2'S,4'S) or (1S,2R,4R,1'S,2'R,4'R) and (1R,2S,4S,1'R,2'S,4'S).

EFFECT: compound is of interest as a biologically active substance and hybrid antioxidant, and may be used in medicine.

1 cl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing porphyrins, texaphyrins, bacteriochlorins, chlorines, coproporphyrin I, corrins, corroles, cytoporphyrins, deuteroporphyrins, etioporphyrin I, etioporphyrin III, hematoporphyrins, phaeophorbide a, phaeophorbide b, phorbines, phthalocyanines, phyllochlorins, phylloporphyrins, phytochlorins, phytoporphyrins, protoporphyrins, pyrrochlorins, pyrroporphyrins, rhodochlorins, rhodoporphyrins and uroporphyrin I, which can be used in the pharmaceutical industry. The disclosed method involves a step (a) for producing a reaction system from reagents in a reaction medium which, under certain conditions and through reactions involving ring formation, can form a macrocycle and undesirable oligomers through oligomerisation reactions; a step (b) for modulating the oligomerisation reactions in the reaction medium with reduction of formation and/or release of undesirable oligomers compared to corresponding unmodulated oligomerisation reactions, by adding to the reaction medium additives which regulate oligomerisation, which contain oligomerisation by-products added from the outside, selected from water, methanol, ethanol, propanol, butanol, alkylthiol, thiophenol, ammonia, methylamine, ethylamine, propylamine, butylamine, dimethylamine, diethylamine and dipropylamine.

EFFECT: novel method of producing the said macrocycles.

33 cl, 19 ex, 26 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing indene dimmers through catalytic dimerisation of indene, characterised by that the catalyst used is zeolite ZSM-12 in H-form in amount of 10-30 wt % and the reaction is carried out at 100-200°C in aliphatic hydrocarbons in ratio indene: solvent equal to 1:1-4 (vol).

EFFECT: method simplifies production of indene dimers.

1 cl, 1 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing indene oligomers through catalytic oligomerisation of indene, characterised by that the catalysts used are zeolites Y and Beta, taken in amount of 10-30 wt % with respect to indene. The reaction is carried out at 80-200°C in a solvent medium or without.

EFFECT: method simplifies production of indene oligomers.

3 cl, 13 ex, 1 tbl

The invention relates to a method of producing bicyclobutane, which is a component of fuel for liquid rocket engines

FIELD: chemistry.

SUBSTANCE: present invention relates to a method of preparing a catalyst complex of formula , where R1, R2, R3 and R4 are independently selected from a group consisting of hydrogen, C1-C20alkyl, C2-C20alkoxy group, halogen and amino group, where if R1 or R3 is an amino group, the amino group is optionally substituted with one or more fragments which are alkyl, if R2 or R4 is an amino group, the amino group is optionally substituted with one or more fragments which are C1-C20alkyl. The method includes a step of reacting a ruthenium catalyst precursor with one or two bidentate ligands of the Schiff base class in a nonpolar solvent and in the presence of a weak base, where the bidentate ligands of the Schiff base class are independently in amount of 1.0-3.0 equivalents relative to the amount of the catalyst precursor (formulae of the precursors and ligands are given in claim 1 of the invention). The invention also discloses a catalyst complex, a supported catalyst for metathesis of olefins and use thereof in olefin metathesis reactions.

EFFECT: invention enables to obtain a catalyst having high activity after activation, monomer stability and a simple and cheap method.

11 cl, 2 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing pentacyclo[8.4.0.03.7.04.14.06.11]tetradeca-8,12-diene of formula The method is characterised by catalytic dimerisation of 1,3,5-cycloheptatriene (CHT). The catalyst used is Ni(acac)2-Et2AlCl. The reaction is carried out with molar ratio CHT:Ni(acac)2:Et2AlCl=10:(0.1-0.3):4, in an argon atmosphere, at 20-100°C, in benzene for 8-48 hours.

EFFECT: method enables to obtain the end product separately.

7 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to the field of organic chemistry, in particular to a method of obtaining alkylethers of 1- and 2-naphthalenecarboxylic acids, which are used in the synthesis of herbicides, plant growth hormones, dyes, photomaterials and polymers. The method of obtaining compounds of formula (1a-b) or (2a-b) in which R=CH3, C2H5, n-C3H7,consists in the fact that naphthalene is subjected to interaction with CCl4 and alcohol (methanol, ethanol, n-propanol) in the presence of metallic iron, activated HCl, and acetylacetone with the molar ratio of [Fe0(met.)]:[acetylacetone]:[naphthalene]:[CCl4]:[alcohol]=5-50:5:100:100-1000:100-1000, at a temperature of 130°C for 4-12 h in the argon atmosphere.

EFFECT: total output of alkyl ethers of 1- and 2-naphthalenecarboxylic acids reaches 75%.

1 tbl, 21 ex

FIELD: chemistry.

SUBSTANCE: method involves catalytic telomerisation of butadiene with diethylamine in the presence of a catalyst based on cationic complexes of palladium (II) of general formula [(acac)Pd(L)2]BF4 (where acac is an acetylacetonate ligand, L=PPh3, P'Pr3, P"Bu3 P(p-Tol)3 or (L)2=diphosphine ligands, selected from bis(diphenylphosphino)methane(dppm), bis(diphenylphosphino)propane(dppp), bis(diphenylphosphino)butane(dppb), bis(diphenylphosphino)ferrocene(dppf)). The process is carried out in a substrate medium, specifically diethylamine and butadiene, at temperature of 50-90°C. The method enables to obtain N,N-diethylocta-2,7-diene-1-amine with selectivity of 99.9% from the overall mixture of reaction products with high process output which reaches 4180 g of product per 1 g Pd. The catalysts used are more readily available compared to those previously used for the process.

EFFECT: improved method.

1 tbl, 1 ex

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