Method for preparing n2, n2, n6, n6-tetraalkyl-4a,5,7a,8-tetrahydro-1,3-diphenylalumina[3,4-f]isoaluminaindol-2,6-(4h,7h)-diamines

FIELD: chemistry of metalloorganic compounds, chemical technology.

SUBSTANCE: invention relates to organic synthesis, namely, to a method for synthesis of novel organoaluminum compounds. Method involves interaction of phenylallylacetylene with dialkylaminoaluminum dichloride in the presence of metallic magnesium and zircocene dichloride as a catalyst, in argon atmosphere at room temperature, in tetrahydrofuran medium for 8-12 h. Invention provides simplifying method and using available reagents.

EFFECT: improved method of synthesis.

1 tbl, 11 ex

 

The present invention relates to methods for new alyuminiiorganicheskikh compounds (AOC), particularly to a method of obtaining the N2N2N6N6-tetraalkyl-4a,5,7a,8-tetrahydro-1,3-diphenylalanine[3,4-f]isoluminance-2,6-(4H,7H)-diamines of General formula (1):

These compounds may find application as components of catalytic systems in the processes of oligomerization and polymerization of olefins and diene hydrocarbons, as well as in industrial thin organic and ORGANOMETALLIC synthesis.

The known method [U.M.Dzhemilev, A.G.Ibragimov, A.B.Morozov. Regio - and Stereoselective Synthesis of trans-3,4-Dialylsubstituted Aluminacyclopentanes in the Presence of Cp2ZrCl2. Mendeleev Commun, 1992, No. 1, P.26-28] obtain 1-(dialkylamino)-TRANS-3,4-dialkylamides of aluminosilicates (2) interaction α-olefins with Diethylaminoethanol (Et2NAlCl2in the presence of magnesium metal (powder) and catalyst Cp2ZrCl2(5 mol.%) at a temperature of 20°8 hours in THF with the release of ˜70% scheme:

The known method does not allow to obtain the N2N2N6N6-tetraalkyl-4A,5,7a,8-tetrahydro-1,3-diphenylalanine[3,4-f]isoluminance-2,6-(4H,7H)-diamines (1).

Thus, in the literature there are no data on regioselective synthesis of N2N N6N6-tetraalkyl-4a,5,7a,8-tetrahydro-1,3-diphenylalanine[3,4-f]isoluminance-2,6-(4H,7H)-diamines of General formula (1).

We propose a new method for the synthesis of N2N2N6N6-tetraalkyl-4a,5,7a,8-tetrahydro-1,3-diphenylalanine[3,4-f]isoluminance-2,6-(4H,7H)-diamines (1).

The method consists in the interaction of phenylethylamine with dialkylaminoalkyl General formula (R2NAlCl2), where R=C2H5The h4H9the h6H13and metal magnesium (powder) in the presence of a catalyst of zirconatetitanate Cp2ZrCl2,taken in a molar ratio of PhC≡CLO2CH=CH2:R2NAlCl2:Mg:Cp2ZrCl2=10:(10-14):(10-14):(0.8-1.2), preferably 10:12:12:1. The reaction is carried out in an argon atmosphere at room temperature (˜20°C) and atmospheric pressure. The reaction time is 8-12 hours, the yield of the target products 57-79%. As a solvent it is necessary to use tetrahydrofuran (THF), in other ethereal solvents (ether, dioxane) output target product (1) is significantly reduced.

The reaction proceeds according to the scheme:

The reaction is accompanied by release equimolar number MgCl2. Target products (1) are formed only with the participation of phenylethylamine, dialkylaminoalkyl R2 NAlCl2where R=C2H5H-C4H9the h6H13metallic Mg as an acceptor halide ions and catalyst Cp2ZrCl2. In the presence of other acetylenes (e.g., dealkylation, dearylation), other compounds of aluminum (for example, Et2AlCl, Et3Al, ISO-Bu3Al, ISO-Bu3AlCl, ISO-Bu2AlH) or other transition metal complexes (for example, Zr(acac)4Cp2TiCl2Pd(acac)2, Ni(acac)2, Fe(ASAS)2target products (1) are not formed.

Conducting the reaction in the presence of a catalyst Cp2ZrCl2more than 12 mol.% in relation to phenylethylamine not lead to a significant increase of the yield of the target products (1). Use in the reaction of the catalyst Cp2ZrCl2less than 8 mol.% reduces the release of AOC (1), which is associated with a reduction of catalytically active sites in the reaction mass. Experiments were performed at room temperature ˜20°C. At higher temperatures (for example, 50° (C) increases the amount of seal products, at a lower temperature (e.g., 0° (C) decreases the reaction rate.

Changing the ratio of initial reagents in the direction of increasing the content of R2NAlCl2or Mg in relation to phenylethylamine does not lead to a significant increase in the yield of target products (1). The decrease in the number of R 2NAlCl2or Mg in relation to phenylethylamine reduces the output of the AOC (1).

The essential difference between the proposed method:

The proposed method is based on using as starting reagent phenylethylamine, and in a known way as a source of unsaturated compounds used α-olefin, causing the formation of 1-(diethylamino)-3,4-dialkylaminomethyl (2).

The proposed method has the following advantages:

The method allows to obtain high regiospecificity N2N2N6N6-tetraalkyl-4A,5,7a,8-tetrahydro-1,3-diphenylalanine[3,4-f]solumina-indole-2,6-(4H,7H)-diamines (1), the synthesis of which are not described in literature.

The method is illustrated by the following examples:

EXAMPLE 1. In a glass reactor with a volume of 50 ml, mounted on a magnetic stirrer, an argon atmosphere was placed 10 ml of tetrahydrofuran, 1 mmol Cp2ZrCl210 mmol of phenylethylamine, 12 g-at. Mg (powder) and at a temperature of ˜0°12 mmol of diethylaminosalicylaldehyde Et2NAlCl2. Stirred at room temperature for 10 hours. Receive individual N2N2N6N6-tetraethyl-4A,5,7a,8-tetrahydro-1,3-diphenyl-alumina[3,4-f]isoluminance-2,6-(4H,7H)-diamine (1). The yield of the target product was determined by the hydrolysis product. When the hydrolysis AOC (1, formed 1,2-dimethyl-4,5-bis[phenylmethylene]cyclohexane (5) with the release of ˜67%, and at lateralize respectively 1,2-bis[watermeter]-4,5-bis[1-phenyl-1-deutero-methylidene]cyclohexane (6).

The spectral characteristics of the products of hydrolysis (5) and laterality (6).

An NMR spectrum1H (CDCl3that δ, ppm) 1,2-dimethyl-4,5-bis[phenylmethylene]cyclohexane (5): 0.87 m (6N, CH3), 1.18-1.28 (m 2H, CH), 1.60 (4H, CH2), 6.89 (2H, =CH), 7.05-7.30 m (10H, CH arene.).

An NMR spectrum13With (δ, ppm) 1,2-dimethyl-4,5-bis[phenylmethylene]cyclohexane (5): 15.26, 26.57, 32.82, 116.25, 127.76, 128.21, 128.73, 131.60, 136.73.

An NMR spectrum1H (CDCl3that δ, ppm): 1,2-bis[watermeter]-4,5-bis[1-phenyl-1-dearomatisation]cyclohexane (6): 0.87 m (4H, CH2D), 1.16-1.28 (m 2H, CH), 1.60 (4H, CH2), 7.00-7.30 m (10H, CH arene.).

An NMR spectrum13With (δ, ppm): 1,2-bis[watermeter]-4,5-bis[1-phenyl-1-dearomatisation]cyclohexane (6): 15.06 so (J20.0 Hz), 26.57, 32.82, 115.95 t (J23.5 Hz), 127.76, 128.21, 128.73, 131.60, 136.73.

Other examples of the method are given in table 1.

Table 1
№№ p/pR2NAlCl2The molar ratio of PhC=CCH2CHCH2:R2NAlCl2:Mg:Cp2ZrCl2mmolReaction time, hoursOutput (1), %
1Et2NalCl210:12:12:11067
210:14:12:11072
310:10:12:11063
410:12:14:11069
510:12:10:11062
610:12:12:1.21079
710:12:12:0.81057
810:12:12:11270
910:12:12:1861
10n-Bu2NalCl210:12:12:11064
11N-Hex2NAlCl210:12:12:11059

All experiments were performed at room temperature (˜20° (C) in tetrahydrofuran. In other ethereal solvents (ether, dioxane) output target product (1) is significantly reduced.

The method of obtaining the N2N2N6N6-tetraalkyl-4A,5,7a,8-tetrahydro-1,3-diphenylol is mine[3,4-f]isoluminance-2,6-(4H,7H)-diamines of General formula

characterized in that phenylethylamine General formula (PhC≡CLO2CH=CH2) interacts with dialkylaminoalkyl (R2NalCl2), where R represents a C2H5H-C4H9the h6H13and metallic magnesium in the presence of a catalyst of zirconatetitanate (Cp2ZrCl2) in a molar ratio of PhC≡CCH2CH=CH2:R2NAlCl2:Mg:Cp2ZrCl2=10:(10-14):(10-14):(0.8-1.2) in an argon atmosphere at normal pressure in tetrahydrofuran for 8-12 hours



 

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EFFECT: improved method of synthesis.

1 tbl, 12 ex

FIELD: chemistry of metalloorganic compounds, chemical technology.

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EFFECT: improved method of synthesis.

1 tbl, 11 ex

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