RU2478615C2 - METHOD OF PRODUCING 1'-[2"-(METHYLTHIO)ETHYL]- 1'-[S-ALKYLCARBOTHIOYL]-(C60-Ih)[5,6]FULLERO[2',3':1,9]CYCLOPROPANES - Google Patents

METHOD OF PRODUCING 1'-[2"-(METHYLTHIO)ETHYL]- 1'-[S-ALKYLCARBOTHIOYL]-(C60-Ih)[5,6]FULLERO[2',3':1,9]CYCLOPROPANES Download PDF

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RU2478615C2
RU2478615C2 RU2011124653/04A RU2011124653A RU2478615C2 RU 2478615 C2 RU2478615 C2 RU 2478615C2 RU 2011124653/04 A RU2011124653/04 A RU 2011124653/04A RU 2011124653 A RU2011124653 A RU 2011124653A RU 2478615 C2 RU2478615 C2 RU 2478615C2
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fullero
ethyl
alkylcarbothioyl
cyclopropanes
methylthio
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Усеин Меметович Джемилев
Айрат Рамилевич Туктаров
Артур Альбертович Хузин
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Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран
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Abstract

FIELD: chemistry.
SUBSTANCE: invention relates to organic synthesis, and specifically to a method of producing sulphur-containing fullerene derivatives of general formula (1): R=Am, i-Pr, Cy, Bn, which involves reaction of C60-fullerene with diazothioates of formula N2(CH2CH2SMe)C(O)SR (R = Am, i-Pr, Cy, Bn) in o-dichlorobenzene, taken in molar ratio C60: diazo-compound = 0.01:(0.02-0.05), at temperature of 80°C for 0.5-1.5 hours.
EFFECT: method of obtaining novel sulphur-containing fullerene derivatives, which can be used as effective nanocomponent additives for industrial oil, as well as novel optoelectronic materials.
1 cl, 1 tbl

Description

Предлагаемое изобретение относится к области органическогоThe present invention relates to the field of organic

синтеза, а именно к способу получения 1'-[2"-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih][5,6]фуллеро[2',3':1,9]циклопропанов общей формулы (1)synthesis, namely, to a method for producing 1 '- [2 "- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ] [5,6] fullero [2 ', 3': 1 , 9] cyclopropanes of the general formula (1)

Figure 00000001
Figure 00000001

Серосодержащие производные фуллеренов могут найти применение в качестве эффективных нанокомпонентных присадок к индустриальным маслам, а также новых материалов для оптоэлектроники (У.М.Джемилев, Г.Н.Кириченко, В.И.Глазунова, А.Г.Ибрагимов, А.Р.Туктаров, М.Пудас, А.А.Десяткин, Н.Р.Поподько, В.В.Королев. Патент РФ №2382816 от 27.02.10, Бюл. №6 [1], А.Р.Туктаров, А.Р.Ахметов, Г.Н.Кириченко, В.И.Глазунова, Л.М.Халилов, У.М.Джемилев. Журн. прикл. хим., 2010, 83, 1132 [2], A.Cravino, N.S.Sariciftci. J.Mater. Chem., 2002, 12, 1931 [3]).Sulfur derivatives of fullerenes can be used as effective nanocomponent additives for industrial oils, as well as new materials for optoelectronics (U.M.Dzhemilev, G.N. Kirichenko, V.I. Glazunova, A.G. Ibrahimov, A.R. Tuktarov, M. Pudas, A. A. Desyatkin, N. P. Popodko, V. V. Korolev, RF Patent No. 2382816 dated 02.27.10, Bull. No. 6 [1], A. R. Tuktarov, A. R. .Akhmetov, G.N. Kirichenko, V.I. Glazunova, L.M. Khalilov, U.M. Dzhemilev.Journal prikl. Chem., 2010, 83, 1132 [2], A. Cravino, NSSariciftci. J. Mater. Chem., 2002, 12, 1931 [3]).

Известен способ (L. Isaacs, A. Wehtsig, F. Diederich. Helv. Chem.Acta. 1993, 76, 1231 [4]) совместного получения 1'-этилформил-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропана (2) и смеси стереоизомерных 1'а-этилформил-1'а-карба-1'(2')а-гомо(С60-Ih)[5,6]фуллеренов (3,4) с суммарным выходом 35% реакцией С60-фуллерена (5) с диазоуксусным эфиром при температуре 110°С в течение 7 чA known method (L. Isaacs, A. Wehtsig, F. Diederich. Helv. Chem.Acta. 1993, 76, 1231 [4]) for the joint production of 1'-ethyl formyl- (C 60 -I h ) [5,6] fullero [2 ', 3': 1.9] cyclopropane (2) and a mixture of stereoisomeric 1'a-ethylformyl-1'a-carba-1 '(2') a-homo (C 60 -I h ) [5,6 ] fullerenes (3.4) with a total yield of 35% by reaction of C 60- fullerene (5) with diazoacetate at a temperature of 110 ° C for 7 hours

Figure 00000002
Figure 00000002

Известный способ не позволяет получать 1'-[2"-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропаны общей формулы (1).The known method does not allow to obtain 1 '- [2 "- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero [2 ', 3': 1,9 ] cyclopropanes of the general formula (1).

Известен способ (A.Skiebe, A.Hirsch. J.Chem.Soc., Chem.Commun., 1994, 335 [5]) получения смеси метано- (6) и стереоизомерных гомофуллеренов (7,8) с общим выходом 20-30% реакцией С60-фуллерена (5) с диазоамидами в кипящем толуоле в течение 48 чA known method (A. Skiebe, A. Hirsch. J. Chem. Soc., Chem. Commun., 1994, 335 [5]) to obtain a mixture of methano- (6) and stereoisomeric homofullerenes (7.8) with a total yield of 20- 30% reaction of C 60 fullerene (5) with diazoamides in boiling toluene for 48 hours

Figure 00000003
Figure 00000003

Известный способ не позволяет получать 1'-[2"-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропаны общей формулы (1).The known method does not allow to obtain 1 '- [2 "- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero [2 ', 3': 1,9 ] cyclopropanes of the general formula (1).

Таким образом, в литературе отсутствуют сведения по селективному синтезу 1'-[2"-(метилтио)этил]-1'-[8-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропанов (1).Thus, in the literature there is no information on the selective synthesis of 1 '- [2 "- (methylthio) ethyl] -1' - [8-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero [2 ', 3 ': 1.9] cyclopropanes (1).

Предлагается новый способ получения 1'-[2"-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih][5,6]фуллеро[2',3':1,9]циклопропанов (1).A new method is proposed for the preparation of 1 '- [2 "- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ] [5,6] fullero [2 ', 3': 1,9] cyclopropanes (1).

Сущность способа заключается во взаимодействии фуллерена (С60) с диазотиоатами формулы N2(CH2CH2SMe)C(O)SR (R=Am, i-Pr, Cy, Bn) в о- дихлорбензоле при мольном соотношении С60: диазотиоат = 0.01:(0.02-0.05), предпочтительно 0.01:0.03 при 80°С в течение 0.5-1.5 ч. Получают 1'-[2"-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропаны (1) с выходом 30-50%. Реакции протекают по схемеThe essence of the method consists in the interaction of fullerene (C 60 ) with diazothioates of the formula N 2 (CH 2 CH 2 SMe) C (O) SR (R = Am, i-Pr, Cy, Bn) in o-dichlorobenzene with a molar ratio of C 60 : diazothioate = 0.01: (0.02-0.05), preferably 0.01: 0.03 at 80 ° C. for 0.5-1.5 hours. 1 '- [2 "- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero [2 ', 3': 1.9] cyclopropanes (1) with a yield of 30-50%. The reactions proceed according to the scheme

Figure 00000004
Figure 00000004

Диазотиоаты берут с избытком по отношению к фуллерену С60 с целью повышения выхода целевых продуктов (1). Снижение количества диазосоединения по отношению к С60 нецелесообразно, так как приводит к уменьшению выхода целевого продукта.Diazothioates are taken in excess with respect to fullerene C 60 in order to increase the yield of target products (1). The decrease in the number of diazocompounds with respect to C 60 is impractical, since it leads to a decrease in the yield of the target product.

1'-[2"-(Метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро-[2',3':1,9]циклопропаны (1) образуются только с участием фуллерена[60] и диазотиоатов.1 '- [2 "- (Methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero- [2 ', 3': 1,9] cyclopropanes (1 ) are formed only with the participation of fullerene [60] and diazotioates.

Проведение реакции при более высокой температуре (например, 100°С) связано с увеличением энергозатрат, при меньшей температуре (например, 40 и 20°С) приводит к снижению селективности реакции, а именно образованию смеси соотвествующих метанофуллеренов (1) и стереоизомерных гомофуллеренов.Carrying out the reaction at a higher temperature (for example, 100 ° C) is associated with an increase in energy consumption; at a lower temperature (for example, 40 and 20 ° C), the selectivity of the reaction is reduced, namely, the formation of a mixture of the corresponding methanofullerenes (1) and stereoisomeric homofullerenes.

Существенные отличия предлагаемого способаSignificant differences of the proposed method

Предлагаемый способ базируется на использовании в качестве исходного реагента диазотиоатов. В известном способе диазоуксусные эфиры и диазоамиды. Предлагаемый способ, в отличие от известных, позволяет селективно получать 1'-[2"-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропаны (1), синтез которых в литературе не описан.The proposed method is based on the use of diazothioates as a starting reagent. In the known method, diazoacetic esters and diazoamides. The proposed method, unlike the known ones, allows one to selectively obtain 1 '- [2 "- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero [2 ', 3 ': 1.9] cyclopropanes (1), the synthesis of which is not described in the literature.

Способ поясняется примерами.The method is illustrated by examples.

К раствору 0.01 ммоля С60-фуллерена в 1.5 мл о-дихлорбензола, нагретого до 80°С, по каплям добавляют 0.03 ммолей диазотиоата в 0.5 мл о-дихлорбензола. Через 1 ч реакционную массу охлаждают и пропускают через колонку с небольшим слоем силикагеля. Получают 1'-[2"-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропаны (1) с выходом 50-60% (по данным ВЭЖХ).To a solution of 0.01 mmol C 60 -fullerene in 1.5 ml of o-dichlorobenzene heated to 80 ° C, 0.03 mmol of diazothioate in 0.5 ml of o-dichlorobenzene was added dropwise. After 1 h, the reaction mass is cooled and passed through a column with a small layer of silica gel. Obtain 1 '- [2 "- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero [2 ', 3': 1,9] cyclopropanes (1 ) with a yield of 50-60% (according to HPLC).

Спектральные характеристики (1)Spectral characteristics (1)

Figure 00000005
Figure 00000005
Выход 55%. Спектр ЯМР 1Н: 1.01 (т, 3Н, СН3, J=6.8 Гц), 1.40-1.55 (м, 4Н, 2СН2), 1.81 (м, 2Н, СН2), 2.30 (с, 3Н, СН3), 3.12 (м, 2Н, СН2), 3.23 (м, 2Н, СН2), 3.25 (т, 2Н, СН2, J=7.2 Гц).Yield 55%. 1 H NMR spectrum: 1.01 (t, 3H, CH 3 , J = 6.8 Hz), 1.40-1.55 (m, 4H, 2CH 2 ), 1.81 (m, 2H, CH 2 ), 2.30 (s, 3H, CH 3 ), 3.12 (m, 2H, CH 2 ), 3.23 (m, 2H, CH 2 ), 3.25 (t, 2H, CH 2 , J = 7.2 Hz). Спектр ЯМР 13С: 14.32, 16.39, 22.64, 29.50, 30.41, 30.86, 31.29, 31.56, 56.03, 75.97, 137.60, 138.08, 140.97, 141.24, 142.10, 142.14, 142.19, 142.28, 142.93, 143.03, 143.13, 143.25, 143.72, 143.94, 144.37, 144.71, 144.88, 145.14, 145.24, 145.26, 145.29, 145.31, 145.60, 145.62, 147.51, 192.60. 13 C NMR spectrum: 14.32, 16.39, 22.64, 29.50, 30.41, 30.86, 31.29, 31.56, 56.03, 75.97, 137.60, 138.08, 140.97, 141.24, 142.10, 142.14, 142.19, 142.28, 142.93, 143.03, 143.13, 143.25, 143.72 , 143.94, 144.37, 144.71, 144.88, 145.14, 145.24, 145.26, 145.29, 145.31, 145.60, 145.62, 147.51, 192.60.
Figure 00000006
Figure 00000006
 Выход 50%. Спектр ЯМР 1H: 1.58 (д, 6Н, 2СН3, J=7.2 Гц), 2.30 (с, 3Н, СН3), 3.11 (м, 2Н, СН2), 3.23 (м, 2Н, СН3), 3.98 (м, 1Н, СН).Yield 50%. 1 H NMR spectrum: 1.58 (d, 6H, 2CH 3 , J = 7.2 Hz), 2.30 (s, 3H, CH 3 ), 3.11 (m, 2H, CH 2 ), 3.23 (m, 2H, CH 3 ), 3.98 (m, 1H, CH). Спектр ЯМР 13С: 16.56, 23.17, 30.94, 31.72, 36.71, 56.12, 76.01, 137.59, 138.06, 140.98, 141.27, 142.11, 142.16, 142.22, 142.31, 142.94, 143.05, 143.15, 143.27, 143.73, 143.96, 144.38, 144.72, 144.89, 145.16, 145.24, 145.26, 145.30, 145.32, 145.61, 145.65, 147.61, 192.02. 13 C NMR spectrum: 16.56, 23.17, 30.94, 31.72, 36.71, 56.12, 76.01, 137.59, 138.06, 140.98, 141.27, 142.11, 142.16, 142.22, 142.31, 142.94, 143.05, 143.15, 143.27, 143.73, 143.96, 144.38, 144.72 , 144.89, 145.16, 145.24, 145.26, 145.30, 145.32, 145.61, 145.65, 147.61, 192.02.

Figure 00000007
Figure 00000007
Выход 60%. Спектр ЯМР 1H: 1.43 и 1.73 (оба м, 2Н, CH2), 1.63 (м, 2Н, СН2), 1.67 (м, 2Н, СН2), 1.85 (м, 2Н, СН2), 2.15 (м, 2Н, СН2), 2.30 (с, 3Н, СН3), 3.10 (м, 2Н, СН2), 3.24 (м, 2Н, СН2), 3.86 (м, 1Н, СН).Yield 60%. 1 H NMR Spectrum: 1.43 and 1.73 (both m, 2H, CH 2 ), 1.63 (m, 2H, CH 2 ), 1.67 (m, 2H, CH 2 ), 1.85 (m, 2H, CH 2 ), 2.15 ( m, 2H, CH 2 ), 2.30 (s, 3H, CH 3 ), 3.10 (m, 2H, CH 2 ), 3.24 (m, 2H, CH 2 ), 3.86 (m, 1H, CH). Спектр ЯМР 13С: 16.53, 26.14, 26.60, 30.92, 31.68, 33.39, 44.29, 56.19, 76.05, 137.57, 138.06, 140.96, 141.25, 142.11, 142.16, 142.21, 142.30, 142.93, 143.04, 143.14, 143.26, 143.73, 143.95, 144.36, 144.71, 144.89, 145.16, 145.23, 145.25, 145.29, 145.62, 145.66, 147.63, 192.50. 13 C NMR spectrum: 16.53, 26.14, 26.60, 30.92, 31.68, 33.39, 44.29, 56.19, 76.05, 137.57, 138.06, 140.96, 141.25, 142.11, 142.16, 142.21, 142.30, 142.93, 143.04, 143.14, 143.26, 143.73, 143.95 , 144.36, 144.71, 144.89, 145.16, 145.23, 145.25, 145.29, 145.62, 145.66, 147.63, 192.50.
Figure 00000008
Figure 00000008
 Выход 52%. Спектр ЯМР 1Н: 2.21 (с, 3Н, СН3), 3.02 (м, 2Н, СН2), 3.18 (м, 2Н, СН2), 4.45 (с, 2Н, СН2), 7.28-7.40 (м, 5Н, 5СН).Yield 52%. 1 H NMR spectrum: 2.21 (s, 3H, CH 3 ), 3.02 (m, 2H, CH 2 ), 3.18 (m, 2H, CH 2 ), 4.45 (s, 2H, CH 2 ), 7.28-7.40 (m 5H, 5CH). Спектр ЯМР 13С: 16.41, 30.83, 31.53, 34.73, 55.71, 75.86, 127.88, 128.88, 129.17, 136.87, 137.64, 138.11, 140.98, 141.26, 142.08, 142.12, 142.20, 142.29, 142.94, 143.03, 143.14, 143.18, 143.26, 143.72, 143.95, 144.38, 144.72, 144.85, 144.89, 145.10, 145.24, 145.26, 145.30, 145.52, 145.56, 147.27, 191.95. 13 C NMR spectrum: 16.41, 30.83, 31.53, 34.73, 55.71, 75.86, 127.88, 128.88, 129.17, 136.87, 137.64, 138.11, 140.98, 141.26, 142.08, 142.12, 142.20, 142.29, 142.94, 143.03, 143.14, 143.18, 143.26 , 143.72, 143.95, 144.38, 144.72, 144.85, 144.89, 145.10, 145.24, 145.26, 145.30, 145.52, 145.56, 147.27, 191.95.

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

Таблица 1Table 1 № п/пNo. p / p RR Мольное соотношение С60: диазотиоат, ммольThe molar ratio of C 60 : diazothioate, mmol Время реакции, чReaction time, h Выход целевых продуктов (1), %The yield of target products (1),%   AmAm       1one   0.01:0.030.01: 0.03 1one 5555 22   0.01:0.020.01: 0.02 1one 4949 33   0.01:0.050.01: 0.05 1one 5757 4four   0.01:0.030.01: 0.03 0.50.5 50fifty 55   0.01:0.030.01: 0.03 1.51.5 5656 66 i-Pri-pr 0.01:0.030.01: 0.03 1one 50fifty 77 CyCy 0.01:0.030.01: 0.03 1one 6060 88 BnBn 0.01:0.030.01: 0.03 1one 5252

Реакции проводили при температуре 80°С в о-дихлорбензоле в качестве растворителя.The reaction was carried out at a temperature of 80 ° C in o-dichlorobenzene as a solvent.

Claims (1)

Способ получения 1'-[2''-(метилтио)этил]-1'-[S-алкилкарботиоил]-(С60-Ih)[5,6]фуллеро[2',3':1,9]циклопропанов общей формулы (1):
Figure 00000009

характеризующийся тем, что С60-фуллерен взаимодействует с диазотиоатами формулы N2(CH2CH2SMe)C(O)SR (R=Am, i-Pr, Су, Bn) в о-дихлорбензоле, взятыми в мольном соотношении С60:диазосоединение=0,01:(0,02-0,05), при температуре 80°С в течение 0,5-1,5 ч. The method of obtaining 1 '- [2''- (methylthio) ethyl] -1' - [S-alkylcarbothioyl] - (C 60 -I h ) [5,6] fullero [2 ', 3': 1,9] cyclopropanes general formula (1):
Figure 00000009

characterized in that the C 60 fullerene interacts with diazothioates of the formula N 2 (CH 2 CH 2 SMe) C (O) SR (R = Am, i-Pr, Cy, Bn) in o-dichlorobenzene taken in a molar ratio of C 60 : diazo compound = 0.01: (0.02-0.05), at a temperature of 80 ° C for 0.5-1.5 hours
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