RU2192424C1 - Method of synthesis of optically active dimeric complexes of (1s,2s)-1,7,7-trimethyl-2-[(dialkyl-alumina)oxy]- bicyclo[2,2,1]heptanes - Google Patents
Method of synthesis of optically active dimeric complexes of (1s,2s)-1,7,7-trimethyl-2-[(dialkyl-alumina)oxy]- bicyclo[2,2,1]heptanes Download PDFInfo
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- RU2192424C1 RU2192424C1 RU2001109192A RU2001109192A RU2192424C1 RU 2192424 C1 RU2192424 C1 RU 2192424C1 RU 2001109192 A RU2001109192 A RU 2001109192A RU 2001109192 A RU2001109192 A RU 2001109192A RU 2192424 C1 RU2192424 C1 RU 2192424C1
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000003786 synthesis reaction Methods 0.000 title abstract description 10
- 230000015572 biosynthetic process Effects 0.000 title abstract description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 241000723346 Cinnamomum camphora Species 0.000 claims abstract description 6
- 229960000846 camphor Drugs 0.000 claims abstract description 6
- 229930008380 camphor Natural products 0.000 claims abstract description 6
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012300 argon atmosphere Substances 0.000 claims abstract description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000001686 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one Substances 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 3
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 3
- 125000002524 organometallic group Chemical group 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 abstract 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- UMRZSTCPUPJPOJ-UHFFFAOYSA-N norbornane Chemical class C1CC2CCC1C2 UMRZSTCPUPJPOJ-UHFFFAOYSA-N 0.000 description 11
- -1 Alkylaluminium Alkoxides Chemical class 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002370 organoaluminium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
Изобретение относится к способам получения новых производных алюминия, конкретно к способу получения оптически активных димерных комплексов (1S, 2S)-1,7,7-триметил-2-[(диалкилалюмина)окси] бицикло[2.2.1] гептанов общей формулы (I):
где R = С2Н5, н-С3Н7, i-С4Н9.The invention relates to methods for producing new derivatives of aluminum, specifically to a method for producing optically active dimeric complexes (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylalumin) oxy] bicyclo [2.2.1] heptanes of the general formula (I ):
where R = C 2 H 5 , nC 3 H 7 , i-C 4 H 9 .
Предлагаемый способ может найти применение в тонком органическом и металлорганическом синтезе, в частности при получении энантиомерно чистых продуктов с высокими оптическими выходами. The proposed method can find application in fine organic and organometallic synthesis, in particular in the production of enantiomerically pure products with high optical yields.
Известен способ ([1] G. Giacomelli, L. Bertero, L. Lardicci. Nickel Catalyzed Stereodifferentiating Displacement Reaction Between Prochiral 1 - Alkenes and Optically Active Organoaluminium Solvates// Tetrahedron Lett., v. 22, 1981, p. 883-886) получения оптически активных алюминийорганических соединений (2) взаимодействием дизамещенных терминальных алкенов с триизобутилалюминием в присутствии Ni-содержащих катализаторов и хиральных лигандов при комнатной температуре в течение 40 ч по схеме 1 (см. в конце описания). The known method ([1] G. Giacomelli, L. Bertero, L. Lardicci. Nickel Catalyzed Stereodifferentiating Displacement Reaction Between Prochiral 1 - Alkenes and Optically Active Organoaluminium Solvates // Tetrahedron Lett., V. 22, 1981, p. 883-886 ) obtaining optically active organoaluminum compounds (2) by reacting disubstituted terminal alkenes with triisobutylaluminum in the presence of Ni-containing catalysts and chiral ligands at room temperature for 40 hours according to Scheme 1 (see the end of the description).
Известным способом не могут быть получены оптически активные димерные комплексы (1S,2S)-1,7,7-триметил-2-[(диалкилалюмина)окси]бицикло[2.2.1]гептанов (1). In a known manner, optically active dimeric complexes of (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylalumin) oxy] bicyclo [2.2.1] heptanes (1) cannot be obtained.
Известен способ ([2] M.L. Sierra, R. Kumar, V. Srini, J. Mel, J.P. Oliver. Synthesis and Spectroscopic Investigations of Alkylaluminium Alkoxides Derived from Optically Active Alcohols// Organometallics, v. l1, 1992, р. 206-214) получения оптически активных алкоксидов алюминия (3) взаимодействием триалкилаланов с оптически активным спиртом при комнатной температуре по схеме 2 (см. в конце описания). The known method ([2] ML Sierra, R. Kumar, V. Srini, J. Mel, JP Oliver. Synthesis and Spectroscopic Investigations of Alkylaluminium Alkoxides Derived from Optically Active Alcohols // Organometallics, v. L1, 1992, p. 206- 214) obtaining optically active aluminum alkoxides (3) by the interaction of trialkylalanes with optically active alcohol at room temperature according to Scheme 2 (see the end of the description).
Известный способ не позволяет получать оптически активные димерные комплексы (1S,2S)-1,7,7-триметил-2-[(диалкилалюмина)окси]бицикло[2.2.1]гептанов (1). The known method does not allow to obtain optically active dimeric complexes of (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylalumin) oxy] bicyclo [2.2.1] heptanes (1).
Таким образом, в литературе совершенно отсутствуют сведения по региоселективному синтезу оптически активных димерных комплексов (1S,2S)-1,7,7-триметил-2-[(диалкилалюмина)окси]бицикло[2.2.1] гептанов (1). Thus, in the literature there is absolutely no information on the regioselective synthesis of optically active dimeric complexes (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylalumin) oxy] bicyclo [2.2.1] heptanes (1).
Предлагается способ получения новых типов оптически активных алюминийорганических соединений, а именно, димерных комплексов (1S,2S)-1,7,7-триметил-2-[(диалкилалюмина)окси]бицикло[2.2.1]гептанов (1). A method is proposed for producing new types of optically active organoaluminum compounds, namely, dimeric complexes (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylalumin) oxy] bicyclo [2.2.1] heptanes (1).
Предлагаемый способ осуществляется взаимодействием (1S,2S)-1,7,7-триметил-бицикло[2.2.1]гептан-2-она (камфоры) с диалкилгидридами алюминия НАlR2 (R = С2Н5, н-С3Н7, i-C4H9), взятыми в мольном соотношении 10:(10-12), предпочтительно 10:11, в атмосфере аргона при комнатной температуре (~20oС) и нормальном давлении в бензоле. Время реакции 0,5-1,5 ч, предпочтительно 1 ч. Выход димерных комплексов (1S,2S)-1,7,7-триметил-2-[(диалкилалюмина)окси] бицикло[2.2.1] гептанов 82-98%. Реакция протекает по схеме 3 (см. в конце описания).The proposed method is carried out by the interaction of (1S, 2S) -1,7,7-trimethyl-bicyclo [2.2.1] heptan-2-one (camphor) with dialkylhydrides of aluminum HAlR 2 (R = C 2 H 5 , n-C 3 N 7 , iC 4 H 9 ), taken in a molar ratio of 10: (10-12), preferably 10:11, in an argon atmosphere at room temperature (~ 20 ° C) and normal pressure in benzene. The reaction time is 0.5-1.5 hours, preferably 1 hour. The yield of dimer complexes (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylaluminium) oxy] bicyclo [2.2.1] heptanes 82-98 % The reaction proceeds according to scheme 3 (see the end of the description).
Оптически активные димерные комплексы (1S, 2S)-1,7,7-триметил-2-[(диалкилалюмина)окси] бицикло[2.2.1] гептанов (1) образуются только лишь с участием (1S,2S)-1,7,7-триметил-бицикло[2.2.1]гептан-2-она и диалкилгидридов алюминия HAlR2. В присутствии других хиральных кетонов или других соединений алюминия (например, АlЕt3, АlВui 3, Et2AlCl, EtAlCl2) целевые продукты (1) не образуются.Optically active dimeric complexes (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylalumin) oxy] bicyclo [2.2.1] heptanes (1) are formed only with the participation of (1S, 2S) -1,7 , 7-trimethyl-bicyclo [2.2.1] heptan-2-one and aluminum dialkyl hydrides HAlR 2 . In the presence of other chiral ketones or other aluminum compounds (e.g. AlEt 3 , AlBu i 3 , Et 2 AlCl, EtAlCl 2 ), the desired products (1) are not formed.
Изменение соотношения исходных реагентов в сторону увеличения содержания HAlR2 по отношению к камфоре не приводит к дальнейшему повышению выхода целевых продуктов (1). Синтезы осуществляли при комнатной температуре (~ 20oС). При более высокой температуре (например, 40oС) не наблюдается увеличение выхода целевых продуктов, а при меньшей температуре (например, 0oС) снижается скорость реакции.A change in the ratio of the starting reagents in the direction of increasing the HAlR 2 content with respect to camphor does not lead to a further increase in the yield of the target products (1). The syntheses were carried out at room temperature (~ 20 o C). At a higher temperature (for example, 40 o C) there is no increase in the yield of the target products, and at a lower temperature (for example, 0 o C) the reaction rate decreases.
Существенные отличия предлагаемого способа:
1. В предлагаемом способе используются в качестве исходных реагентов диалкилалюминийгидриды (HAlR2) и оптически активный кетон (камфора). В известном способе применяются в качестве исходных реагентов триалкилаланы (AlR3) и оптически активный спирт.Significant differences of the proposed method:
1. In the proposed method, dialkylaluminum hydrides (HAlR 2 ) and optically active ketone (camphor) are used as starting reagents. In the known method, trialkylalanes (AlR 3 ) and optically active alcohol are used as starting reagents.
Предлагаемый способ обладает следующими преимуществами:
1. Способ позволяет получать с высокой региоселективностью оптически активные димерные комплексы (1S,2S)-1,7,7-триметил-2-[(диалкилалюмина)окси]бицикло[2.2.1]гептанов (1), синтез которых в литературе не описан.The proposed method has the following advantages:
1. The method allows to obtain with high regioselectivity optically active dimeric complexes (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylaluminium) oxy] bicyclo [2.2.1] heptanes (1), the synthesis of which is not available in the literature described.
Способ поясняется следующими примерами:
Пример 1. В стеклянный реактор объемом 50 мл, установленный на магнитной мешалке, в атмосфере аргона помещают 11 ммолей HAl(i-Bu)2 в 9 мл С6Н6. К данной смеси небольшими порциями добавляют 10 ммолей (1S,2S)-1,7,7-триметил-бицикло[2.2.1] гептан-2-она(камфора), перемешивают 1 ч при комнатной температуре (~20oС). Получают димер (1S,2S)-1,7,7-триметил-2-[(диизобутилалюмина)окси] бицикло[2.2.1] гептана с выходом 94%. [α]
Example 1. In a 50 ml glass reactor mounted on a magnetic stirrer, 11 mmol of HAl (i-Bu) 2 in 9 ml of C 6 H 6 are placed in an argon atmosphere. To this mixture, 10 mmoles of (1S, 2S) -1,7,7-trimethyl-bicyclo [2.2.1] heptan-2-one (camphor) are added in small portions, stirred for 1 h at room temperature (~ 20 ° C). A dimer of (1S, 2S) -1,7,7-trimethyl-2 - [(diisobutylaluminium) oxy] bicyclo [2.2.1] heptane is obtained in a yield of 94%. [α]
Спектр ЯМР 13С димера (1S,2S)-1,7,7-триметил-2-[(диизобутилалюмина)окси] бицикло[2.2.1]гептана (δ, м.д., 22,5 МГц, С6D6):
Другие примеры, подтверждающие способ, приведены в табл. 1. 13 C NMR spectrum of (1S, 2S) -1,7,7-trimethyl-2 - [(diisobutylaluminium) oxy] bicyclo [2.2.1] heptane dimer (δ, ppm, 22.5 MHz, C 6 D 6 ):
Other examples confirming the method are given in table. 1.
Claims (1)
где R= С2Н5, н-С3Н7, i-C4H9,
отличающийся тем, что (1S, 2S)-1,7,7-триметилбицикло[2.2.1] гептан-2-он (камфора) взаимодействует с диалкилгидридами алюминия HAlR2, R определено выше, при мольном соотношении 10: (10-12) в атмосфере аргона при комнатной температуре (~ 20oC) и нормальном давлении в среде бензола в течение 0,5 - 1,5 ч.A method of obtaining optically active dimeric complexes of (1S, 2S) -1,7,7-trimethyl-2 - [(dialkylalumin) oxy] -bicyclo [2.2.1] heptanes of the general formula I (see graphic part),
where R = C 2 H 5 , nC 3 H 7 , iC 4 H 9 ,
characterized in that (1S, 2S) -1,7,7-trimethylbicyclo [2.2.1] heptan-2-one (camphor) interacts with aluminum dialkyl hydrides HAlR 2 , R as defined above, with a molar ratio of 10: (10-12 ) in an argon atmosphere at room temperature (~ 20 o C) and normal pressure in benzene for 0.5 to 1.5 hours
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2373212C2 (en) * | 2007-10-23 | 2009-11-20 | Институт нефтехимии и катализа РАН | Method of producing optically active (1r,2s,5r)-[[5-methyl-2-(1-methylethyl)cyclohexyl]oxy] dichloralane |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0342444A2 (en) * | 1988-05-19 | 1989-11-23 | MERCK PATENT GmbH | Cyclical organic-metal compounds |
| RU2079499C1 (en) * | 1994-11-22 | 1997-05-20 | Институт общей и неорганической химии им.Н.С.Курнакова РАН | Method for production of complex compound of aluminium with tetra-crawn-phthalocyanine |
| RU2139880C1 (en) * | 1998-04-30 | 1999-10-20 | Институт нефтехимии и катализа АН Республики Башкортостан | Method of preparing 2-chloro-2-alumabicyclo [3,2,2,] nonane |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0342444A2 (en) * | 1988-05-19 | 1989-11-23 | MERCK PATENT GmbH | Cyclical organic-metal compounds |
| RU2079499C1 (en) * | 1994-11-22 | 1997-05-20 | Институт общей и неорганической химии им.Н.С.Курнакова РАН | Method for production of complex compound of aluminium with tetra-crawn-phthalocyanine |
| RU2139880C1 (en) * | 1998-04-30 | 1999-10-20 | Институт нефтехимии и катализа АН Республики Башкортостан | Method of preparing 2-chloro-2-alumabicyclo [3,2,2,] nonane |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2373212C2 (en) * | 2007-10-23 | 2009-11-20 | Институт нефтехимии и катализа РАН | Method of producing optically active (1r,2s,5r)-[[5-methyl-2-(1-methylethyl)cyclohexyl]oxy] dichloralane |
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