RU2714319C1 - Method for selective production of substituted 1-styryl-2-hydrofullerenes - Google Patents

Method for selective production of substituted 1-styryl-2-hydrofullerenes Download PDF

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RU2714319C1
RU2714319C1 RU2019125877A RU2019125877A RU2714319C1 RU 2714319 C1 RU2714319 C1 RU 2714319C1 RU 2019125877 A RU2019125877 A RU 2019125877A RU 2019125877 A RU2019125877 A RU 2019125877A RU 2714319 C1 RU2714319 C1 RU 2714319C1
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substituted
hydrofullerenes
styryl
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etmgbr
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Усеин Меметович Джемилев
Айрат Рамилевич Туктаров
Нури Мамедеевич Чобанов
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Федеральное государственное бюджетное научное учреждение Уфимский федеральный исследовательский центр Российской академии наук
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    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
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Abstract

FIELD: chemistry.
SUBSTANCE: invention relates to organic chemistry and specifically to a method for selective production of substituted 1-styryl-2-hydrofullerenes of general formula 1:
Figure 00000016
Method involves reaction of C60-fullerene with substituted arylacetylenes of general formula
Figure 00000017
where X=H, o-F, m-F, p-Cl, p-Me, in chlorobenzene in the presence of EtMgBr and Ti(OiPr)4, taken in molar ratio C60 : arylacetylene : Ti(OiPr)4 : EtMgBr = 1:(2–4):(1–3):(8–12), at temperature of 20–80 °C for 10–50 minutes.
EFFECT: obtaining substituted 1-styryl-2-hydrofullerenes of general formula 1, which can find application of materials with given electronic, magnetic properties, as well as components of modern solar panels and field-effect transistors.
1 cl, 2 ex, 1 tbl

Description

Предлагаемое изобретение относится к области органического синтеза, а именно, к способу селективного получения замещенных 1-стирил-2-гидрофуллеренов общей формулы 1:The present invention relates to the field of organic synthesis, and in particular, to a method for the selective preparation of substituted 1-styryl-2-hydrofullerenes of the general formula 1:

Figure 00000001
Figure 00000001

Углеродные кластеры, содержащие в своем составе π-сопряженные системы, являются перспективными соединениями при создании новых материалов с заданными электронными, магнитными и оптическими свойствами, а также в качестве компонентов современных солнечных батарей и полевых транзисторов. (Л.Н. Сидоров, М.А. Юровская, А.Я. Борщевский, И.В. Трушков, И.Н. Иоффе. Фуллерены: Учебное пособие, М.: Издательство «Экзамен», 2005, 688 с [1].Carbon clusters containing π-conjugated systems are promising compounds for creating new materials with specified electronic, magnetic and optical properties, as well as components of modern solar cells and field effect transistors. (L.N. Sidorov, M.A. Yurovskaya, A.Ya. Borschevsky, I.V. Trushkov, I.N. ].

Известен способ (Y. Murata, K. Motoyama et all. Tetrahedron 1996, 52, 5077 [2]) получения смеси моно- (4) и бис-аддукта (5) с выходом 45 и 16%, соответственно, реакцией С60-фуллерена (2) с избытком [(триметилсилил)этинил]лития (3) в толуоле при кипячении.A known method (Y. Murata, K. Motoyama et all. Tetrahedron 1996, 52, 5077 [2]) to obtain a mixture of mono (4) and bis adduct (5) with a yield of 45 and 16%, respectively, by reaction With 60 - fullerene (2) with an excess of [(trimethylsilyl) ethynyl] lithium (3) in toluene during boiling.

Figure 00000002
Figure 00000002

Известный способ не позволяет селективно получать замещенные 1-стирил-2-гидрофуллерены общей формулы 1.The known method does not allow to selectively receive substituted 1-styryl-2-hydrofullerenes of General formula 1.

Известен способ (М. Lamrani, R. Hamasaki, М. Mitsuishi, М. Miyashta, Y. Yamamoto. Chem. Commun, 2000, 1595 [3]) получения фенилэтинилгидрофуллеренов 8 реакцией замещенных арилацетиленов 6 и BuLi 7 с С60-фуллереном 2 в кипящем толуоле.A known method (M. Lamrani, R. Hamasaki, M. Mitsuishi, M. Miyashta, Y. Yamamoto. Chem. Commun, 2000, 1595 [3]) for the production of phenylethynyl hydrofullerenes 8 by reaction of substituted aryl acetylenes 6 and BuLi 7 with C 60- fullerene 2 in boiling toluene.

Figure 00000003
Figure 00000003

Известный способ не позволяет селективно получать замещенные 1-стирил-2-гидрофуллерены общей формулы 1.The known method does not allow to selectively receive substituted 1-styryl-2-hydrofullerenes of General formula 1.

Таким образом, в литературе отсутствуют сведения по синтезу замещенных 1-стирил-2-гидрофуллеренов общей формулы 1.Thus, in the literature there is no information on the synthesis of substituted 1-styryl-2-hydrofullerenes of the general formula 1.

Предлагается новый способ получения замещенных 1-стирил-2-гидрофуллеренов (1).A new method is proposed for producing substituted 1-styryl-2-hydrofullerenes (1).

Сущность способа заключается во взаимодействии фуллерена (С60) (2) с замещенными арилацетиленами 9 общей формулы

Figure 00000004
где Х=Н, o-F, m-F, р-Cl, p-Ме, в хлорбензоле в присутствии EtMgBr и Ti(OiPr)4, взятыми в мольном соотношении С60 : арилацетилен : Ti(OiPr)4:EtMgBr=1:(2-4):(1-3):(8-12), предпочтительно 1:3:2.5:10, при температуре 20-80°С в течение 10-50 мин. Получают замещенные 1-стирил-2-гидрофуллерены 1 с выходом 10-75%. Реакция протекает по схеме:The essence of the method consists in the interaction of fullerene (C 60 ) (2) with substituted aryl acetylenes 9 of the general formula
Figure 00000004
where X = H, oF, mF, p-Cl, p-Me, in chlorobenzene in the presence of EtMgBr and Ti (OiPr) 4 , taken in a molar ratio of C 60 : aryl acetylene: Ti (OiPr) 4 : EtMgBr = 1: (2 -4) :( 1-3) :( 8-12), preferably 1: 3: 2.5: 10, at a temperature of 20-80 ° C for 10-50 minutes. Substituted 1-styryl-2-hydrofullerenes 1 are obtained in 10-75% yield. The reaction proceeds according to the scheme:

Figure 00000005
Figure 00000005

Проведение указанной реакции в присутствии титанового катализатора [Ti] больше 2.5-кратного избытка по отношению к фуллерену С60 не приводит к существенному увеличению выхода целевого продукта (1). Применение титанового катализатора [Ti] в количестве меньше 2.5-кратного избытка по отношению к фуллерену С60 снижает выход целевого продукта, что связано с образованием побочных продуктов в виде аддуктов карбомагнирования. Проведение реакции при более высокой температуре (например, 100-120°С) не целесообразно, поскольку приводит к увеличению энергозатрат, при меньшей температуре (например, -20°С) снижается скорость реакции.Carrying out this reaction in the presence of a titanium catalyst [Ti] more than a 2.5-fold excess with respect to fullerene C 60 does not significantly increase the yield of the target product (1). The use of a titanium catalyst [Ti] in an amount of less than 2.5-fold excess with respect to fullerene C 60 reduces the yield of the target product, which is associated with the formation of by-products in the form of carbomagnetization adducts. Carrying out the reaction at a higher temperature (for example, 100-120 ° C) is not advisable, since it leads to an increase in energy consumption, at a lower temperature (for example, -20 ° C), the reaction rate decreases.

Существенные отличия предлагаемого способа:Significant differences of the proposed method:

Предлагаемый способ базируется на использовании в качестве катализатора исключительно Ti(Oi-Pr)4. Предлагаемый способ, в отличие от известных, является более энергоэффективным и позволяет получать замещенные 1 -стирил-2-гидрофуллерены 1 с достаточно высокими выходами и селективностью, синтез которых в литературе не описан.The proposed method is based on the use of exclusively Ti (Oi-Pr) 4 as a catalyst. The proposed method, in contrast to the known ones, is more energy efficient and allows to obtain substituted 1-styryl-2-hydrofullerenes 1 with sufficiently high yields and selectivity, the synthesis of which is not described in the literature.

Способ поясняется примерами.The method is illustrated by examples.

Пример 1. К раствору 40 мг (0.1112 ммолей) С60-фуллерена в 12 мл сухого хлорбензола в атмосфере аргона последовательно добавляют фенилацетилен (0.3336 ммолей) и 0.08 мл (0.278 ммолей) Ti-катализатора. К реакционной массе по каплям добавляют 1.1 мл (1.112 ммолей) 1 М раствора EtMgBr в диэтиловом эфире. Через 30 мин реакционную массу обрабатывают 5%-ным водным раствором HCl. Органический слой пропускают через колонку с небольшим слоем силикагеля. Получают замещенные 1-стирил-2-гидрофуллерены с выходом 66-75% (по данным ВЭЖХ).Example 1. To a solution of 40 mg (0.1112 mmol) of 60- fullerene in 12 ml of dry chlorobenzene in an argon atmosphere, phenylacetylene (0.3336 mmol) and 0.08 ml (0.278 mmol) of Ti-catalyst are successively added. 1.1 ml (1.112 mmol) of a 1 M solution of EtMgBr in diethyl ether are added dropwise to the reaction mass. After 30 min, the reaction mass is treated with 5% aqueous HCl. The organic layer is passed through a column with a small layer of silica gel. Substituted 1-styryl-2-hydrofullerenes are obtained in a yield of 66-75% (according to HPLC).

Спектральные характеристикиSpectral characteristics

Figure 00000006
Figure 00000006

Выход 75%. Спектр ЯМР 1Н (500 MHz, CDCl3 и CS2=1:5): 6.73 (с, 1Н, С60-Н), 7.42 (т, 1Н, СН (Ph), J=7.5 Hz), 7.51 (т, 2Н, 2СН (Ph), J=7.5 Hz), 7.55 (д, 1H, CH, J=17 Hz), 7.76(д, 2H, 2CH (Ph), J=7.5 Hz), 7.93(д, 1H, CH, J=17 Hz). ЯМР 13C (125 MHz, CDCl3 и CS2=1:5): 61.13, 66.26, 127.18, 128.67, 129.14, 131.32, 135.99, 136.06, 136.44, 136.56, 140.49, 141.82, 142.19, 142.32, 142.76, 143.38, 144.73, 144.85, 145.53, 145.67, 145.75, 145.89, 146.26, 146.32, 146.38, 146.51, 146.56, 146.96, 147.44, 147.62, 152.67, 153.37. MALDI-TOF: найдено 824.0625 [M]+, вычислено 824.0626 для C68H8 Yield 75%. 1 H NMR spectrum (500 MHz, CDCl 3 and CS 2 = 1: 5): 6.73 (s, 1H, C 60 -H), 7.42 (t, 1H, CH (Ph), J = 7.5 Hz), 7.51 ( t, 2H, 2CH (Ph), J = 7.5 Hz), 7.55 (d, 1H, CH, J = 17 Hz), 7.76 (d, 2H, 2CH (Ph), J = 7.5 Hz), 7.93 (d, 1H, CH, J = 17 Hz). 13 C NMR (125 MHz, CDCl 3 and CS 2 = 1: 5): 61.13, 66.26, 127.18, 128.67, 129.14, 131.32, 135.99, 136.06, 136.44, 136.56, 140.49, 141.82, 142.19, 142.32, 142.76, 143.38, 144.73, 144.85, 145.53, 145.67, 145.75, 145.89, 146.26, 146.32, 146.38, 146.51, 146.56, 146.96, 147.44, 147.62, 152.67, 153.37. MALDI-TOF: found 824.0625 [M] + , calculated 824.0626 for C 68 H 8

Пример 2. Аналогично примеру 1, но с использованием других арилацетиленов.Example 2. Analogously to example 1, but using other aryl acetylenes.

Спектральные характеристикиSpectral characteristics

Figure 00000007
Figure 00000007

Выход 67%. Спектр ЯМР 1Н (500 MHz, CDCl3 и CS2=1:5): 6.74 (с, 1Н, С60-Н), 7.21 (д, 1H, CH (Ph), J=7.5 Hz), 7.32 (д, 1Н, CH (Ph), J=7.5 Hz), 7.42 (т, 1H, CH, J=7.5 Hz), 7.65 (д, 1H, CH (Ph), J=15.5 Hz), 7.85 (т, 1H, CH (Ph), J=7.5 Hz), 8.07 (д, 1H, CH, J=15.5 Hz). ЯМР 13C (125 MHz, CDCl3 и CS2=1:5): 61.06, 66.57, 116.24, 116.42, 124.17, 124.68, 124.81, 128.52, 129.09, 129.88, 129.94, 136.18, 136.56, 138.73, 138.78, 140.52, 141.84, 141.87, 142.17, 142.21, 142.31, 142.77, 143.18, 143.37, 144.72, 144.85, 145.53, 145.57, 145.66, 145.79, 145.89, 146.22, 146.33, 146.38, 146.52, 146.57, 146.95, 147.62, 152.55, 153.00. MALDI-TOF: найдено 841.0483 [M-H]-, вычислено 842.0532 для C68H7FYield 67%. 1 H NMR spectrum (500 MHz, CDCl 3 and CS 2 = 1: 5): 6.74 (s, 1H, C 60 -H), 7.21 (d, 1H, CH (Ph), J = 7.5 Hz), 7.32 ( d, 1H, CH (Ph), J = 7.5 Hz), 7.42 (t, 1H, CH, J = 7.5 Hz), 7.65 (d, 1H, CH (Ph), J = 15.5 Hz), 7.85 (t, 1H, CH (Ph), J = 7.5 Hz), 8.07 (d, 1H, CH, J = 15.5 Hz). 13 C NMR (125 MHz, CDCl 3 and CS 2 = 1: 5): 61.06, 66.57, 116.24, 116.42, 124.17, 124.68, 124.81, 128.52, 129.09, 129.88, 129.94, 136.18, 136.56, 138.73, 138.78, 140.52, 141.84, 141.87, 142.17, 142.21, 142.31, 142.77, 143.18, 143.37, 144.72, 144.85, 145.53, 145.57, 145.66, 145.79, 145.89, 146.22, 146.33, 146.38, 146.52, 146.57, 146.95, 147.62, 152. MALDI-TOF: found 841.0483 [MH] - , calculated 842.0532 for C 68 H 7 F

Figure 00000008
Figure 00000008

Выход 70%. Спектр ЯМР 1Н (500 MHz, CDCl3 и CS2=1:5): 6.72 (с, 1H, С60-Н), 7.12 (т, 1Н, СН (Ph), J=8 Hz), 7.48-7.56 (м, 4Н, 3СН (Ph), СН), 7.95 (д, 1Н, СН, J=15.5 Hz). ЯМР 13С (125 MHz, CDCl3 и CS2=1:5): 60.99, 66.14, 113.56, 113.73, 115.39, 115.56, 123.09, 130.15, 130.56, 130.62, 136.13, 136.49, 137.32, 138.80, 138.86, 140.53, 141.82, 141.87, 142.14, 142.18, 142.21, 142.29, 142.79, 143.38, 144.70, 144.86, 145.53, 145.58, 145.68, 145.79, 145.87, 146.15, 146.34, 146.39, 146.54, 146.57, 146.91, 147.45, 147.64, 152.49, 152.93, 162.36, 164.33. MALDI-TOF: найдено 841.0498 [M-H]+, вычислено 842.0532 для C68H7FYield 70%. 1 H NMR spectrum (500 MHz, CDCl 3 and CS 2 = 1: 5): 6.72 (s, 1H, C 60 -H), 7.12 (t, 1H, CH (Ph), J = 8 Hz), 7.48- 7.56 (m, 4H, 3CH (Ph), CH), 7.95 (d, 1H, CH, J = 15.5 Hz). 13 C NMR (125 MHz, CDCl 3 and CS 2 = 1: 5): 60.99, 66.14, 113.56, 113.73, 115.39, 115.56, 123.09, 130.15, 130.56, 130.62, 136.13, 136.49, 137.32, 138.80, 138.86, 140.53, 141.82, 141.87, 142.14, 142.18, 142.21, 142.29, 142.79, 143.38, 144.70, 144.86, 145.53, 145.58, 145.68, 145.79, 145.87, 146.15, 146.34, 146.39, 146.54, 146.57, 146.91, 147.45, 147.64, 147.64, 159.44 162.36, 164.33. MALDI-TOF: found 841.0498 [MH] + , calculated 842.0532 for C 68 H 7 F

Figure 00000009
Figure 00000009

Выход 68%. Спектр ЯМР 1Н (500 MHz, CDCl3 и CS2=1:5): 6.71 (с, 1H, С60-Н), 7.42 (д, 2Н, 2СН (Ph), J=8 Hz), 7.52 (д, 1Н, СН, J=16 Hz), 7.71 (д, 2H, 2СН (Ph), J=8 Hz), 7.93 (д, 1H, CH, J=16 Hz). ЯМР 13C (125 MHz, CDCl3 и CS2=1:5): 61.00, 66.18, 128.32, 129.33, 130.03, 134.65, 134.94, 136.09, 136.48, 136.67, 140.51, 141.81, 141.86, 142.17, 142.29, 142.78, 143.38, 144.70, 144.85, 145.53, 145.57, 145.67, 145.77, 145.87, 146.16, 146.34, 146.39, 146.53, 146.57, 146.91, 147.46, 147.64, 152.52, 153.03. MALDI-TOF: найдено 857.0244 [M-H]-, вычислено 858.0236 для C68H7ClYield 68%. 1 H NMR spectrum (500 MHz, CDCl 3 and CS 2 = 1: 5): 6.71 (s, 1H, C 60 -H), 7.42 (d, 2H, 2CH (Ph), J = 8 Hz), 7.52 ( d, 1H, CH, J = 16 Hz), 7.71 (d, 2H, 2CH (Ph), J = 8 Hz), 7.93 (d, 1H, CH, J = 16 Hz). 13 C NMR (125 MHz, CDCl 3 and CS 2 = 1: 5): 61.00, 66.18, 128.32, 129.33, 130.03, 134.65, 134.94, 136.09, 136.48, 136.67, 140.51, 141.81, 141.86, 142.17, 142.29, 142.78, 143.38, 144.70, 144.85, 145.53, 145.57, 145.67, 145.77, 145.87, 146.16, 146.34, 146.39, 146.53, 146.57, 146.91, 147.46, 147.64, 152.52, 153.03. MALDI-TOF: found 857.0244 [MH] - , calculated 858.0236 for C 68 H 7 Cl

Figure 00000010
Figure 00000010

Выход 66%. Спектр ЯМР 1Н (500 MHz, CDCl3 и CS2=1:5): 6.72 (с, 1Н, С60-Н), 7.29 (д, 2Н, 2СН (Ph), J=7.5 Hz), 7.5 (д, 1Н, СН, J=16 Hz), 7.64 (д, 2H, 2СН (Ph), J=8 Hz), 7.87 (д, 1H, CH, J=16 Hz). ЯМР 13C (125 MHz, CDCl3 и CS2=1:5): 61.18, 66.28, 127.16, 129.85, 131.23, 133.69, 135.05, 136.01, 136.58, 138.38, 140.47, 140.50, 141.82, 141.85, 142.20, 142.33, 142.75, 143.18, 143.37, 144.74, 144.85, 145.52, 145.56, 145.65, 145.73, 145.91, 146.31, 146.37, 146.50, 146.56, 146.98, 147.44, 147.61, 152.74, 153.55. MALDI-TOF: найдено 838.0800 [M-H]-, вычислено 838.0782 для С69Н10 Yield 66%. 1 H NMR spectrum (500 MHz, CDCl 3 and CS 2 = 1: 5): 6.72 (s, 1H, C 60 -H), 7.29 (d, 2H, 2CH (Ph), J = 7.5 Hz), 7.5 ( d, 1H, CH, J = 16 Hz), 7.64 (d, 2H, 2CH (Ph), J = 8 Hz), 7.87 (d, 1H, CH, J = 16 Hz). 13 C NMR (125 MHz, CDCl 3 and CS 2 = 1: 5): 61.18, 66.28, 127.16, 129.85, 131.23, 133.69, 135.05, 136.01, 136.58, 138.38, 140.47, 140.50, 141.82, 141.85, 142.20, 142.33, 142.75, 143.18, 143.37, 144.74, 144.85, 145.52, 145.56, 145.65, 145.73, 145.91, 146.31, 146.37, 146.50, 146.56, 146.98, 147.44, 147.61, 152.74, 153.55. MALDI-TOF: found 838.0800 [MH] - , calculated 838.0782 for C 69 H 10

Другие примеры, подтверждающие способ, приведены в табл. 1Other examples confirming the method are given in table. 1

Figure 00000011
Figure 00000011

Реакции проводили в инертной атмосфере при температуре 20-80°С в хлорбензоле в качестве растворителя.The reactions were carried out in an inert atmosphere at a temperature of 20-80 ° C in chlorobenzene as a solvent.

Claims (3)

Способ селективного получения замещенных 1-стирил-2-гидрофуллеренов общей формулы 1:A method for the selective preparation of substituted 1-styryl-2-hydrofullerenes of the general formula 1:
Figure 00000012
Figure 00000012
 характеризующийся тем, что С60-фуллерен взаимодействует с замещенными арилацетиленами общей формулы
Figure 00000013
где Х=Н, o-F, m-F, р-Cl, p-Ме, в хлорбензоле в присутствии EtMgBr и Ti(OiPr)4, взятыми в мольном соотношении С60 : арилацетилен : Ti(OiPr)4 : EtMgBr=1:(2-4):(1-3):(8-12), при температуре 20-80°С в течение 10-50 мин.characterized in that C 60 fullerene interacts with substituted aryl acetylenes of the general formula
Figure 00000013
where X = H, oF, mF, p-Cl, p-Me, in chlorobenzene in the presence of EtMgBr and Ti (OiPr) 4 , taken in a molar ratio of C 60 : aryl acetylene: Ti (OiPr) 4 : EtMgBr = 1: (2 -4) :( 1-3) :( 8-12), at a temperature of 20-80 ° C for 10-50 minutes.
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