SU479772A1 - The method of obtaining 2,3-bis- (o-carboranyl) -butadiene - Google Patents

The method of obtaining 2,3-bis- (o-carboranyl) -butadiene

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Publication number
SU479772A1
SU479772A1 SU1949903A SU1949903A SU479772A1 SU 479772 A1 SU479772 A1 SU 479772A1 SU 1949903 A SU1949903 A SU 1949903A SU 1949903 A SU1949903 A SU 1949903A SU 479772 A1 SU479772 A1 SU 479772A1
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SU
USSR - Soviet Union
Prior art keywords
carboranyl
butadiene
bis
obtaining
product
Prior art date
Application number
SU1949903A
Other languages
Russian (ru)
Inventor
Леонид Иванович Захаркин
Валерий Николаевич Калинин
Наталья Павловна Левина
Original Assignee
Ордена Ленина Институт Элементоорганических Соединений Ан Ссср
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Ордена Ленина Институт Элементоорганических Соединений Ан Ссср filed Critical Ордена Ленина Институт Элементоорганических Соединений Ан Ссср
Priority to SU1949903A priority Critical patent/SU479772A1/en
Application granted granted Critical
Publication of SU479772A1 publication Critical patent/SU479772A1/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

СиSi

НС-с гNS-with g

30-250С30-250С

о/about/

BjoHioBjohio

сн, /оmon, o

4. /С-СН4. / C-CH

с-with-

Выход целевого продукта 60%-80 7оПример . К амиду натри , полученному из 2,3 г Na (0,01 г же) в 300 мл аммиака, при -50° С добавл ют 9,9 г (0,03 моль) 1-(а,р-дибромэтил)-о-карборана в 50 мл абсолютного эфира и смесь перемешивают при (40) - (-60)° С 1,5 час. Затем большую часть аммиака испар ют при кипении и к остатку добавл ют воду. Водный слой экстрагируют эфиром и эфирные выт л ки сушат над хлористым кальцием. После отгонки растворител  остаток кристаллизуют из гексана. Получают 5 г (67%) 1-(а-бромвинил)-о-карборана , т. ил. 60-6ГС.The yield of the target product 60% -80 7oExample. To sodium amide, prepared from 2.3 g of Na (0.01 g of the same) in 300 ml of ammonia, 9.9 g (0.03 mol) of 1- (a, p-dibromoethyl) - o-carboran in 50 ml of absolute ether and the mixture is stirred at (40) - (-60) ° C for 1.5 hours. Then most of the ammonia is evaporated at boiling and water is added to the residue. The aqueous layer is extracted with ether and the ether extracts are dried over calcium chloride. After distilling off the solvent, the residue is crystallized from hexane. 5 g (67%) of 1- (a-bromo-vinyl) -o-carboran, t. Il. 60-6GS.

Найдено, %: С 19,13; Н 5,16; В 43,46; Вг 31,53.Found,%: C 19.13; H 5.16; B 43.46; Br 31.53.

C4Hi3BioBr.C4Hi3BioBr.

,С 19,28; Н 5,26; В 43,49;, C 19.28; H 5.26; B 43.49;

Вычислено, Вг 32,08.Calculated, Br 32.08.

2600 (В-Н), 30802600 (B – H), 3080

- 1- one

ИК-спектр, IR spectrum

см ( С-Н), 1620 (С С).cm (C – H), 1620 (C C).

1-(а-бром7 ,5 г (0,03 моль) полученного экв) меди винил)-о-карборана и 3,2 г (0,05 г нагревают 8 час в пальчиковом автоклаве при 240-250° С. Продукт экстрагируют эфиром . После отгонки эфира остаток перекристаллизовьшают из гептана. Получают 2,5 г (50%) 2,3-бис-(о - карборанил) - бутадиена, т. пл. 304-306° С.1- (a-bromo, 5 g (0.03 mol) of the resulting eq) copper vinyl) -o-carboran and 3.2 g (0.05 g are heated for 8 hours in a finger autoclave at 240-250 ° C. The product is extracted ether. After the ether has been distilled off, the residue is recrystallized from heptane to give 2.5 g (50%) of 2,3-bis- (o-carboranyl) butadiene, mp 304-306 ° C.

Найдено, %: С 28,73; Н 8,25. Мол. вес (масс-спектрометрически) 340.Found,%: C 28.73; H 8.25. Mol weight (mass spectrometrically) 340.

СзНзбВгоВычислено , %: С 28,36; Н 7,75. Мол. вес. 338.SzNzbVgoCalculated,%: C 28.36; H 7.75. Mol weight. 338.

ИК-спектр, 2600 (В-Н), 3070 (С-Н), 1625 (С С-С С).IR Spectrum, 2600 (B – H), 3070 (C – H), 1625 (C C – C C).

Предмет изобретени Subject invention

1.Способ получени  2,3-б«с-(о-карборанил )-бутадиена, отличающийс  тем, что1. A method for producing 2,3-b "c- (o-carboranyl) -butadiene, characterized in that

Claims (3)

1-(а,|3-дибромэтил) -о-карборан подвергают взаимодействию с амидом натри  в среде жид .кого аммиака при охлаждении с последующей обработкой полученного продукта порошком меди при нагревании и выделением целевого продукта известными приемами.1- (a, | 3-dibromoethyl) -o-carborane is reacted with sodium amide in liquid ammonia while cooling, followed by treating the resulting product with copper powder while heating and isolating the target product using known techniques. 2.Способ по п. 1, отличающийс  тем, что охлаждение ведут до (-40) - (-60)° С.2. A method according to claim 1, characterized in that the cooling is carried out to (-40) - (-60) ° C. 3.Способ по пп. 1 и 2, отличающийс  тем, что обработку продукта порошком меди ведут при 230-250° С.3. Method according to paragraphs. 1 and 2, characterized in that the processing of the product with copper powder is carried out at 230-250 ° C.
SU1949903A 1973-07-19 1973-07-19 The method of obtaining 2,3-bis- (o-carboranyl) -butadiene SU479772A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU1949903A SU479772A1 (en) 1973-07-19 1973-07-19 The method of obtaining 2,3-bis- (o-carboranyl) -butadiene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU1949903A SU479772A1 (en) 1973-07-19 1973-07-19 The method of obtaining 2,3-bis- (o-carboranyl) -butadiene

Publications (1)

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SU479772A1 true SU479772A1 (en) 1975-08-05

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Country Status (1)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993008122A1 (en) * 1991-10-23 1993-04-29 Guerbet S.A. Contrast agents and compositions for radiological imaging, and radiological imaging method utilizing same
US5545397A (en) * 1991-10-23 1996-08-13 Boron Biologicals, Inc. Contrast agents and compositions for radiological imaging, and radiological imaging method utilizing same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993008122A1 (en) * 1991-10-23 1993-04-29 Guerbet S.A. Contrast agents and compositions for radiological imaging, and radiological imaging method utilizing same
US5545397A (en) * 1991-10-23 1996-08-13 Boron Biologicals, Inc. Contrast agents and compositions for radiological imaging, and radiological imaging method utilizing same

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