CN104059094A - Synthesis method of 9-borabicyclo[3.3.1]nonane dimer - Google Patents
Synthesis method of 9-borabicyclo[3.3.1]nonane dimer Download PDFInfo
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- CN104059094A CN104059094A CN201410215370.7A CN201410215370A CN104059094A CN 104059094 A CN104059094 A CN 104059094A CN 201410215370 A CN201410215370 A CN 201410215370A CN 104059094 A CN104059094 A CN 104059094A
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Abstract
The invention relates to a synthesis method of a 9-borabicyclo[3.3.1]nonane dimer. The synthesis method is used for synthesizing the 9-borabicyclo[3.3.1]nonane dimer by performing a hydroboration reaction on a hydroboron, an oxidizing agent and 1,5-cyclooctadiene as the raw materials in a solvent selected from ethers, aromatic hydrocarbons, aliphatic hydrocarbons and the like under the protection of an inert gas. The synthesis method is simple and convenient to operate, mild in conditions, low in cost, high in product yield and product purity, and suitable for certain scale industrial production.
Description
Technical field
The present invention relates to the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, belong to organic chemical synthesis field.
Background technology
Borine can carry out various new chemical reaction, has become the reagent of organic synthesis, is widely used in the formation of hydrocarbon key, carbon-oxygen bond, carbonnitrogen bond, carbon-carbon bond.9-boron dicyclo [3.3.1] the nonane dimer of mixing generally exists with the form of crystal or solution.
Soderquist(Simple, remarkably efficient route to high purity, crystalline 9-borabicyclo[3.3.1] nonane (9-BBN) dimer. J.Org.chem.1981,46,4599-4600.) under nitrogen atmosphere, in the ethylene glycol dimethyl ether solution of dimethyl sulphide borine, dropwise add 1,5-cyclooctadiene, 50-60 DEG C of reaction 1h, then at 83-85 DEG C, dimethyl sulphide is removed in vacuum distilling, just can obtain assorted dicyclo [3.3.1] the nonane dimer of 9-boron at 0 DEG C; (the Cyclic Hydrocarbon of 1 such as Knights, 5-Cyclooctadine. A Simple Synthesis of 9-Borabicyclo[3.3.1] nonane, an Unusually Stable Dialkylborane. J.Am.Chem.Soc. 1968,90,5280-5281.) under the condition of ice bath, the tetrahydrofuran solution of 1,5-cyclooctadiene is added drop-wise in borine tetrahydrofuran complex; And then reflux 1h, ice bath is cooling, filters and make assorted dicyclo [3.3.1] the nonane dimer of 9-boron under nitrogen atmosphere.Above synthetic method, raw materials used price is higher, need cryopreservation; And dimethyl sulphide has foul odour, environmental pollution is larger; The loaded down with trivial details harshness of reaction conditions, operation inconvenience, is unfavorable for suitability for industrialized production.
Summary of the invention
The object of the present invention is to provide a kind of 9-boron dimeric synthetic method of dicyclo [3.3.1] nonane of mixing, raw material is cheap, reaction conditions gentleness, easy, safety.
For achieving the above object, the present invention adopts following technical scheme:
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) be in molar ratio 1:(0.3-3) take hydroborate and liquid oxidizer, or take hydroborate and solid oxidizer; Use dissolution with solvents hydroborate, or dissolve respectively hydroborate and solid oxidizer with solvent; Oxidizing agent solution is dropwise joined in hydroborate solution, under protection of inert gas, under room-temperature water bath condition, react, oxidizing agent solution drips off and finishes reaction simultaneously, collects the diborane gas that reaction generates;
(2) diborane step (1) being generated slowly passes into 1; in the ethers mixing solutions of 5-cyclooctadiene and Lewis base; under protection of inert gas; ventilate complete, 40-50 DEG C is continued reacting by heating 1-5 h, finishes reaction; being cooled to room temperature adularescent needle-like crystal separates out; filter, vacuum-drying, obtains assorted dicyclo [3.3.1] the nonane dimer product of 9-boron.
The described hydroborate of step (1) is sodium borohydride, POTASSIUM BOROHYDRIDE or lithium borohydride; Liquid oxidizer is boron trifluoride ethyl ether complex or phosphoric acid; Solid oxidizer is subchloride of mercury or iodine; The mol ratio of hydroborate and boron trifluoride ethyl ether complex is 1:(1.0-3.0), the mol ratio of hydroborate and phosphoric acid is 1:(1.0-3.0), the mol ratio of hydroborate and subchloride of mercury is 1:(0.3-0.6), hydroborate and iodine and mol ratio be 1:(0.3-2.0).
Described hydroborate solvent or the solid oxidizer solvent of step (1) is tetrahydrofuran (THF), glycol dimethyl ether, glycol ether dme, diglycol ethylene dme, normal hexane, benzene or toluene; 1 described mmol hydroborate of step (1) dissolves with hydroborate solvent 0.09-0.5 mL, 0.2-1.0 mL solid-oxide dissolution with solvents for 1 mmol solid-oxide.
The described oxygenant of step (1) drips off time 2-6 h used.
The mol ratio of 1,5-cyclooctadiene and hydroborate is (0.4-1.3): 1.
The described Lewis base of step (2) is DMA, N, N-Diethyl Aniline, tetrahydrofuran (THF), morpholine or pyridine; 1 mmol 1,5-cyclooctadiene need add 0.03-0.25 mL Lewis base.
The described ethers of step (2) is tetrahydrofuran (THF), glycol dimethyl ether, glycol ether dme or diglycol ethylene dme; 1 mmol 1,5-cyclooctadiene need add 0.3-1.5 mL ethers solution.
Step (2) vacuum-drying condition is 50-60 DEG C of vacuum-drying 10-15 h.
Step (1) and (2) described rare gas element are nitrogen or argon gas, and step (1) and (2) described solvent reclaim by underpressure distillation, recycle.
actively useful effect of the present invention:
1. cost of material of the present invention is cheap, and production cost is low;
2. the technology of instantaneous absorption after the present invention adopts diborane to generate, the security that has improved production technique, the suitability for industrialized production of applicable certain scale;
3. solvent for use of the present invention, by recovery, cycling and reutilization, has been realized synthesis technique and the technology of environmental protection.
Brief description of the drawings
Fig. 1 is that assorted dicyclo [3.3.1] nonane of the 9-boron that obtains of embodiment 1 is dimeric
11b NMR figure;
Fig. 2 is that assorted dicyclo [3.3.1] nonane of the 9-boron that obtains of embodiment 1 is dimeric
13c NMR figure;
Fig. 3 is that assorted dicyclo [3.3.1] nonane of the 9-boron that obtains of embodiment 1 is dimeric
1h NMR figure.
Embodiment
Below in conjunction with some specific embodiments, the present invention is further described.
Embodiment 1
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) be that 1:1.5 gets sodium borohydride 2.84 g (75mmol) and boron trifluoride ethyl ether complex 14 mL(113 mmol according to sodium borohydride and boron trifluoride ethyl ether complex mol ratio), with 7 mL diglycol ethylene dme dissolvings, the lower boron trifluoride ethyl ether complex of water-bath dropwise joins in sodium borohydride reaction flask, under nitrogen protection, room temperature 5 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 6 mL (50 mmol) 1; 5-cyclooctadiene, 5 mL(40 mmol) N; in the mixing solutions of accelerine and 30 mL diglycol ethylene dme; under nitrogen protection; ventilate complete; 50 DEG C are continued reacting by heating 3 h; finish reaction; being cooled to room temperature adularescent needle-like crystal separates out; filter, 50 DEG C of vacuum-drying 12 h, obtain assorted dicyclo [3.3.1] nonane dimer 5.0 g of 9-boron; productive rate is 82%, and detected result is referring to Fig. 1-3.
Embodiment 2
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) be that 1:2.0 gets sodium borohydride 2.84 g (75 mmol) and boron trifluoride ethyl ether complex 19 mL(150 mmol according to sodium borohydride and boron trifluoride ethyl ether complex mol ratio), with 9 mL diglycol ethylene dme dissolvings, the lower boron trifluoride ethyl ether complex of water-bath dropwise joins in sodium borohydride reaction flask, under argon shield, room temperature 4 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 6 mL (50 mmol) 1; 5-cyclooctadiene, 5 mL(40 mmol) in the mixing solutions of DMA and 30 mL diglycol ethylene dme, under argon shield; ventilate complete; 50 DEG C are continued reacting by heating 5 h, finish reaction, are cooled to room temperature adularescent needle-like crystal and separate out; filter; 60 DEG C of vacuum-drying 10 h, obtain assorted dicyclo [3.3.1] nonane dimer 4.9 g of 9-boron, and productive rate is 80.3%.
Embodiment 3
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) be that 1:1.5 gets sodium borohydride 2.84 g (75mmol) and boron trifluoride ethyl ether complex 14 mL(113mmol according to sodium borohydride and boron trifluoride ethyl ether complex mol ratio), with 9 mL glycol dimethyl ethers dissolvings, the lower boron trifluoride ethyl ether complex of water-bath dropwise joins in sodium borohydride reaction flask, under nitrogen protection, room temperature 6 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 6 mL (50 mmol) 1; 5-cyclooctadiene, 5 mL(40 mmol) in the mixing solutions of DMA and 30 mL glycol dimethyl ethers, under nitrogen protection; ventilate complete; 45 DEG C are continued reacting by heating 4 h, finish reaction, are cooled to room temperature adularescent needle-like crystal and separate out; filter; 55 DEG C of vacuum-drying 11 h, obtain assorted dicyclo [3.3.1] nonane dimer 5.1 g of 9-boron, and productive rate is 83.6%.
Embodiment 4
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) be that 1:3 gets sodium borohydride 2.84 g (75 mmol) and boron trifluoride ethyl ether complex 28 mL(225 mmol according to sodium borohydride and boron trifluoride ethyl ether complex mol ratio), with 7 mL diglycol ethylene dme dissolvings, the lower boron trifluoride ethyl ether complex of water-bath dropwise joins in sodium borohydride reaction flask, under nitrogen protection, room temperature 5 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 9 mL (75 mmol) 1; 5-cyclooctadiene, 3.5 mL(40 mmol) in the mixing solutions of morpholine and 35 mL diglycol ethylene dme; under nitrogen protection, ventilate complete, 50 DEG C are continued reacting by heating 3 h; finish reaction; be cooled to room temperature adularescent needle-like crystal and separate out, filter 50 DEG C of vacuum-drying 12 h; obtain assorted dicyclo [3.3.1] the nonane dimer 7.4g of 9-boron, productive rate is 85.2%.
Embodiment 5
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) be that 1:1 gets sodium borohydride 2.84 g (75 mmol) and boron trifluoride ethyl ether complex 9 mL(75 mmol according to sodium borohydride and boron trifluoride ethyl ether complex mol ratio), with 7 mL diglycol ethylene dme dissolvings, the lower boron trifluoride ethyl ether complex of water-bath dropwise joins in sodium borohydride reaction flask, under argon shield, room temperature 5 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 12 mL (97.5 mmol) 1; 5-cyclooctadiene, 3.2 mL(40 mmol) in the mixing solutions of pyridine and 30 mL diglycol ethylene dme; under argon shield, ventilate complete, 50 DEG C are continued reacting by heating 3 h; finish reaction; be cooled to room temperature adularescent needle-like crystal and separate out, filter 50 DEG C of vacuum-drying 12 h; obtain assorted dicyclo [3.3.1] nonane dimer 7.2 g of 9-boron, productive rate is 78.7%.
Embodiment 6
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) ratio that is 1:1.5 according to mol ratio is got sodium borohydride 1.55 g (41 mmol) and iodine 15.6 g (61.5 mmol), dissolve with 15 mL diglycol ethylene dme respectively, lower iodine liquid of water-bath dropwise joins in sodium borohydride reaction flask, under nitrogen protection, room temperature 3 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 2.5 mL (20.1 mmol) 1; 5-cyclooctadiene, 4.2 mL(33 mmol) in the mixing solutions of DMA and 30 mL diglycol ethylene dme, under nitrogen protection; ventilate complete; 45 DEG C are continued reacting by heating 2 h, finish reaction, are cooled to room temperature adularescent needle-like crystal and separate out; filter; 55 DEG C of vacuum-drying 12 h, obtain assorted dicyclo [3.3.1] nonane dimer 1.5 g of 9-boron, and productive rate is 61.2%.
Embodiment 7
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) ratio that is 1:1 according to mol ratio takes sodium borohydride 1.55 g (41 mmol) and iodine 10.4 g (41 mmol), dissolve with 20 mL diglycol ethylene dme respectively, lower iodine liquid of water-bath dropwise joins in sodium borohydride reaction flask, under nitrogen protection, room temperature 4 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 5 mL (41 mmol) 1; 5-cyclooctadiene, 4.2 mL(33 mmol) in the mixing solutions of DMA and 30 mL diglycol ethylene dme, under nitrogen protection; ventilate complete; 40 DEG C are continued to add reaction 4 h, finish reaction, are cooled to room temperature adularescent needle-like crystal and separate out; filter; 50 DEG C of vacuum-drying 15 h, obtain assorted dicyclo [3.3.1] nonane dimer 3.2 g of 9-boron, and productive rate is 64%.
Embodiment 8
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) ratio that is 1:2 according to mol ratio takes sodium borohydride 1.55 g (41 mmol) and iodine 20.8 g (82 mmol), with 15 mL glycol dimethyl ethers dissolving sodium borohydrides, with 40 mL diglycol ethylene dme dissolving iodines, lower iodine liquid of water-bath dropwise joins in sodium borohydride reaction flask, under argon shield, room temperature 5 h drip off, and finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 5 mL (41 mmol) 1; 5-cyclooctadiene, 4.2 mL(33 mmol) in the mixing solutions of DMA and 30 mL diglycol ethylene dme, under argon shield; ventilate complete; 50 DEG C are continued reacting by heating 1 h, finish reaction, are cooled to room temperature adularescent needle-like crystal and separate out; filter; 60 DEG C of vacuum-drying 10 h, obtain assorted dicyclo [3.3.1] nonane dimer 2.9 g of 9-boron, and productive rate is 58.5%.
Embodiment 9
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) ratio that is 1:0.3 according to mol ratio takes POTASSIUM BOROHYDRIDE 3.1 g (82 mmol) and iodine 6.2 g (24.6 mmol), by 15 mL diglycol ethylene dme dissolving POTASSIUM BOROHYDRIDE, with 20 mL glycol ether dme dissolving iodines, lower iodine liquid of water-bath dropwise joins in sodium borohydride reaction flask, under nitrogen protection, room temperature 2 h drip off, and finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 5 mL (41 mmol) 1; 5-cyclooctadiene, 4.2 mL(33 mmol) in the mixing solutions of DMA and 30 mL diglycol ethylene dme, under nitrogen protection; ventilate complete; 45 DEG C are continued reacting by heating 2 h, finish reaction, are cooled to room temperature adularescent needle-like crystal and separate out; filter; 55 DEG C of vacuum-drying 12 h, obtain assorted dicyclo [3.3.1] nonane dimer 3.2 g of 9-boron, and productive rate is 64%.
Embodiment 10
The assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron, comprises the following steps:
(1) ratio that is 1:1 according to mol ratio takes sodium borohydride 1.55 g (41 mmol) and iodine 10.4 g (41 mmol), dissolve with 15 mL tetrahydrofuran (THF)s respectively, lower iodine liquid of water-bath dropwise joins in sodium borohydride reaction flask, under nitrogen protection, room temperature 3 h drip off, finish reaction simultaneously, collect the diborane gas that reaction generates;
(2) diborane step (1) being generated passes into 5 mL (41 mmol) 1; 5-cyclooctadiene, 4.2 mL(33 mmol) in the mixing solutions of DMA and 30 mL tetrahydrofuran (THF)s, under nitrogen protection; ventilate complete; 45 DEG C are continued reacting by heating 2 h, finish reaction, are cooled to room temperature adularescent needle-like crystal and separate out; filter; 55 DEG C of vacuum-drying 11 h, obtain assorted dicyclo [3.3.1] nonane dimer 2.8 g of 9-boron, and productive rate is 56%.
Claims (9)
1. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of 9-boron, is characterized in that, comprises the following steps:
(1) be in molar ratio 1:(0.3-3) take hydroborate and liquid oxidizer, or take hydroborate and solid oxidizer; Use dissolution with solvents hydroborate, or dissolve respectively hydroborate and solid oxidizer with solvent; Oxidizing agent solution is dropwise joined in hydroborate solution, under protection of inert gas, under room-temperature water bath condition, react, oxidizing agent solution drips off and finishes reaction simultaneously, collects the diborane gas that reaction generates;
(2) diborane step (1) being generated slowly passes into 1; in the ethers mixing solutions of 5-cyclooctadiene and Lewis base; under protection of inert gas; ventilate complete, 40-50 DEG C is continued reacting by heating 1-5 h, finishes reaction; being cooled to room temperature adularescent needle-like crystal separates out; filter, vacuum-drying, obtains assorted dicyclo [3.3.1] the nonane dimer product of 9-boron.
2. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, is characterized in that, the described hydroborate of step (1) is sodium borohydride, POTASSIUM BOROHYDRIDE or lithium borohydride; Liquid oxidizer is boron trifluoride ethyl ether complex or phosphoric acid; Solid oxidizer is subchloride of mercury or iodine; The mol ratio of hydroborate and boron trifluoride ethyl ether complex is 1:(1.0-3.0), the mol ratio of hydroborate and phosphoric acid is 1:(1.0-3.0), the mol ratio of hydroborate and subchloride of mercury is 1:(0.3-0.6), hydroborate and iodine and mol ratio be 1:(0.3-2.0).
3. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, it is characterized in that, described hydroborate solvent or the solid oxidizer solvent of step (1) is tetrahydrofuran (THF), glycol dimethyl ether, glycol ether dme, diglycol ethylene dme, normal hexane, benzene or toluene; 1 described mmol hydroborate of step (1) dissolves with hydroborate solvent 0.09-0.5 mL, 0.2-1.0 mL solid-oxide dissolution with solvents for 1 mmol solid-oxide.
4. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, is characterized in that, the described oxygenant of step (1) drips off time 2-6 h used.
5. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, is characterized in that, the mol ratio of 1,5-cyclooctadiene and hydroborate is (0.4-1.3): 1.
6. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, is characterized in that, the described Lewis base of step (2) is DMA, N, N-Diethyl Aniline, tetrahydrofuran (THF), morpholine or pyridine; 1 mmol 1,5-cyclooctadiene need add 0.03-0.25 mL Lewis base.
7. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, it is characterized in that, the described ethers of step (2) is tetrahydrofuran (THF), glycol dimethyl ether, glycol ether dme or diglycol ethylene dme; 1 mmol 1,5-cyclooctadiene need add 0.3-1.5 mL ethers solution.
8. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, is characterized in that, step (2) vacuum-drying condition is 50-60 DEG C of vacuum-drying 10-15 h.
9. the assorted dimeric synthetic method of dicyclo [3.3.1] nonane of a kind of 9-boron according to claim 1, it is characterized in that, step (1) and (2) described rare gas element are nitrogen or argon gas, and step (1) and (2) described solvent reclaim by underpressure distillation, recycle.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2018232552A1 (en) * | 2017-06-19 | 2018-12-27 | 陈德如 | Preparation method of bis(3-methyl-2-butyl)borane |
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| RU2265022C1 (en) * | 2004-04-12 | 2005-11-27 | Дзержинский опытный завод авиационных материалов Открытое акционерное общество "Авиабор" | Method for preparing 9-borabicyclo[3,3,1]nonane |
| CN103524541A (en) * | 2013-09-02 | 2014-01-22 | 南开大学 | Preparation method of 9-boron bicyclo (3,3,1)-nonane (9-BBN) |
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| RU2265022C1 (en) * | 2004-04-12 | 2005-11-27 | Дзержинский опытный завод авиационных материалов Открытое акционерное общество "Авиабор" | Method for preparing 9-borabicyclo[3,3,1]nonane |
| CN103524541A (en) * | 2013-09-02 | 2014-01-22 | 南开大学 | Preparation method of 9-boron bicyclo (3,3,1)-nonane (9-BBN) |
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| A. PELTER ET AL.: "Hindered organoboron groups in organic synthesis.15.Preparation and properties of bis(2,4,6-triisopropylphenyl)borane", 《TETRAHEDRON LETTERS 》 * |
| J.SODERQUIST ET AL.: "A Simple, Remarkably Efficient Route to High Purity, Crystalline 9-Borabicyclo[3.3.1]nonane (9-BBN) Dimer", 《J.ORG.CHEM》 * |
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| W. JOHNSON ET AL.: "Cyclic Hydroboration of 1,s-Cyclooctadiene,A Simple Synthesis of 9-Borabicyclo[3.3.1]nonane, an Unusually Stable Dialkylborane", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018232552A1 (en) * | 2017-06-19 | 2018-12-27 | 陈德如 | Preparation method of bis(3-methyl-2-butyl)borane |
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