Trimethylaluminium
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| Names | |
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| IUPAC name
Trimethylalumane
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| Other names
Trimethylaluminum; aluminium trimethyl; aluminum trimethyl
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.000.776 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H18Al2 | |
| Molar mass | 144.17 g/mol 72.09 g/mol (C3H9Al) |
| Appearance | Colorless liquid |
| Density | 0.752 g/cm3 |
| Melting point | 15 °C (59 °F; 288 K) |
| Boiling point | 125–130 °C (257–266 °F; 398–403 K)[1][2] |
| Reacts | |
| Vapor pressure |
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| Viscosity |
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| Thermochemistry | |
Heat capacity (C)
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155.6 J/mol·K[2] |
Std molar
entropy (S⦵298) |
209.4 J/mol·K[2] |
Std enthalpy of
formation (ΔfH⦵298) |
−136.4 kJ/mol[2] |
Gibbs free energy (ΔfG⦵)
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−9.9 kJ/mol[2] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Pyrophoric |
| GHS labelling: | |
  [1]
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| Danger | |
| H250, H260, H314[1] | |
| P222, P223, P231+P232, P280, P370+P378, P422[1] | |
| NFPA 704 (fire diamond) | |
| Flash point | −17.0 °C (1.4 °F; 256.1 K)[1] |
| Related compounds | |
Related compounds
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Triethylaluminium |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trimethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2(CH3)6 (abbreviated as Al2Me6 or TMA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially important compound, closely related to triethylaluminium.[3][4]
Structure and bonding
[edit]The structure and bonding in Al2R6 and diborane are analogous (R = alkyl). In Al2Me6, the Al-C(terminal) and Al-C(bridging) distances are 1.97 and 2.14 Å, respectively. The Al center is tetrahedral.[5] The carbon atoms of the bridging methyl groups are each surrounded by five neighbors: three hydrogen atoms and two aluminium atoms. The methyl groups interchange readily intramolecularly. At higher temperatures, the dimer cracks into monomeric AlMe3.[6]
Synthesis
[edit]TMA is prepared via a two-step process that can be summarized as follows:
- 2 Al + 6 CH3Cl + 6 Na → Al2(CH3)6 + 6 NaCl
A kind of preparation method of trimethyl aluminium
Technical field
The invention belongs to high purity metal organic compound preparation technical field, particularly, relate to a kind of preparation method of trimethyl aluminium.
Background technology
High purity trimethyl aluminium belongs to high-purity metal organic compound, be the critical support starting material utilizing advanced metal organic chemical vapor deposition (MOCVD) technique or atomic layer deposition thin film technology (ALD) to prepare compound semiconductor film material, it is widely used in the fields such as LED device, solar cell of new generation, phase transition storage, semiconductor laser, infrared eye and supercomputer.
The preparation of current trimethyl aluminium has certain research, and common method is magnalium reduction method, aluminum alkyls and haloalkane synthesis method etc.Magnalium reduction method generally adopts magnalium and methyl chloride to carry out reaction to prepare trimethyl aluminium, but this preparation method's yield is extremely low.And aluminum alkyls and haloalkane synthesis method adopt aluminum alkyls (as triethyl aluminum) and methyl halide (as methyl iodide, monobromethane) to synthesize trimethyl aluminium under bismuthino compound or the catalysis of vanadium based compound, but the deficiency such as the method exists that expensive catalyst, yield are not high, the cycle is long and aftertreatment is difficult.
Therefore, be badly in need of now a kind ofly can significantly improving trimethyl aluminium yield and the preparation method that easily reclaims of byproduct of reaction.
Summary of the invention
The object of the invention is the defect reclaimed to overcome the low and byproduct of reaction of trimethyl aluminium yield in prior art difficulty, a kind of preparation method of trimethyl aluminium is provided.
The present inventor finds under study for action, exists and under inert atmosphere, by magnalium and haloalkane contact reacts, obtain trimethyl aluminium ethers title complex at ether solvent; By trimethyl aluminium ethers title complex and high boiling amine and/or phosphines contact reacts, obtain trimethyl aluminium Complexes and/or trimethyl aluminium phosphine class title complex; The title complex obtained is carried out solution join, the yield of trimethyl aluminium, purity can be improved, and the by product of this reaction is comparatively easy to reclaim.
Therefore, to achieve these goals, the invention provides a kind of preparation method of trimethyl aluminium, the method comprises:
(1) exist at ether solvent and under inert atmosphere, by magnalium and haloalkane contact reacts, obtain trimethyl aluminium ethers title complex;
(2) by trimethyl aluminium ethers title complex and high boiling amine and/or phosphines contact reacts, trimethyl aluminium Complexes and/or trimethyl aluminium phosphine class title complex is obtained;
(3) title complex that step (2) obtains is carried out solution to join.
Preparation method of the present invention can significantly improve yield and the purity of trimethyl aluminium, its yield can be made up to more than 80%, high purity 99.9999%, and, the present invention's reactor used can be used as evaporating kettle and uses, simplify technique and equipment, reaction process is easy to control, product also comparatively easy and raw material, the separation of by-products of preparation, be highly suitable for suitability for industrialized production, in addition, its by product can be used for synthesizing Tai-Ace S 150, and almost no waste mine produces.
Other features and advantages of the present invention are described in detail in embodiment part subsequently.
Embodiment
Below the specific embodiment of the present invention is described in detail.Should be understood that, embodiment described herein, only for instruction and explanation of the present invention, is not limited to the present invention.
The invention provides a kind of preparation method of trimethyl aluminium, the method comprises:
(1) exist at ether solvent and under inert atmosphere, by magnalium and haloalkane contact reacts, obtain trimethyl aluminium ethers title complex;
(2) by trimethyl aluminium ethers title complex and high boiling amine and/or phosphines contact reacts, trimethyl aluminium Complexes and/or trimethyl aluminium phosphine class title complex is obtained;
(3) title complex that step (2) obtains is carried out solution to join.
According to method of the present invention, wherein, in step (1), haloalkane can be the various haloalkane in this area, is preferably methyl iodide and/or monobromethane, is more preferably methyl iodide, thus can improve the yield of trimethyl aluminium further, and byproduct of reaction more easily reclaims.
According to method of the present invention, wherein, in step (1), ether solvent can be the alkyl oxide of various routine, such as, can be at least one in ether, tetrahydrofuran (THF) and methyltetrahydrofuran, is preferably methyltetrahydrofuran.
According to method of the present invention, wherein, in step (1), magnalium is Al xmg y, its composition can be x=0.4-0.6, y=0.6-0.4, x+y=1, x, y is massfraction.
According to method of the present invention, wherein, in step (1), in magnalium, the mol ratio of aluminium and haloalkane can be the conventional ratio in this area, is preferably 1:2-12, is more preferably 1:2.5-9.
According to method of the present invention, wherein, the weight ratio of ether solvent and magnalium can be 1:0.1-0.5.
According to method of the present invention, wherein, in step (1), inert atmosphere can be provided by nitrogen, argon gas etc.
According to method of the present invention, wherein, in step (1), contact reacts condition optimization is for comprising: temperature is 20-90 DEG C, and the time is 2-8h, more preferably, temperature is 35-75 DEG C, and the time is 3-6h, thus can improve the yield that can improve trimethyl aluminium further further.
According to method of the present invention, wherein, for the ease of operation, haloalkane can be dripped to containing in the ether solvent of magnalium in step (1), carry out more fully and the potential safety hazard avoided reacting sharply heat release and cause to make reaction, preferably, haloalkane is dripped lentamente to containing in the ether solvent of magnalium under agitation in step (1).In the present invention, the speed dripping haloalkane lentamente can be 2-5ml/min.
According to method of the present invention, wherein, preferably, the solution reactant ligand of step (2) is carried out in step (1) reaction again after terminating.Wherein, the contact reacts due to step (1) is thermopositive reaction, and the terminal that therefore its reaction terminates can by continuing to drip haloalkane in ether solvent, and the temperature of reaction solution no longer raises to judge.
According to method of the present invention, wherein, in order to avoid solvent is on the impact of follow-up solution reactant ligand, the yield of the trimethyl aluminium that final impact is obtained and purity, preferably, steam ether solvent after step (1) reaction terminates, then carry out solution reactant ligand.
According to method of the present invention, wherein, the method can also comprise: trimethyl aluminium ethers title complex step (1) obtained steams at reduced pressure conditions.Wherein, described reduced pressure can comprise: pressure is 0-0.05MPa.
According to method of the present invention, wherein, in step (2), high boiling aminated compounds can be at least one in pentanoic, Tributylamine and trioctylamine, be preferably pentanoic, high boiling phosphines is triphenylphosphine and/or diphenylphosphine, is preferably triphenylphosphine, when adopting triphenylphosphine, the amplitude that the yield of trimethyl aluminium and purity improve is maximum.
According to method of the present invention, wherein, in step (2), preferably, relative to 1mol haloalkane, the consumption of amine and/or phosphines is 0.3-0.8mol.
According to method of the present invention, wherein, in step (2), preferably, catalytic condition comprises: temperature is 20-100 DEG C, and the time is 2-8h.
According to method of the present invention, wherein, preferably, in step (2), by the reaction solution containing trimethyl aluminium Complexes or trimethyl aluminium phosphine class title complex 80-110 DEG C, distill under 0-0.02MPa, this distillation can steam lower boiling impurity and above-mentioned steps (1) reaction terminate after the ether solvent that do not steam completely of distilation steps, thus avoid this lower-boiling impurity and ether solvent on the impact of follow-up solution reactant ligand, and then affect yield and the purity of trimethyl aluminium.
According to method of the present invention, wherein, in step (3), preferably, the solution condition of joining comprises: temperature is 120-200 DEG C, pressure is 0-0.03MPa, and the time is 5-15h, and being preferably temperature is 130-180 DEG C, pressure is 0-0.01MPa, time is 5-12h, thus can make trimethyl aluminium Complexes and/or trimethyl aluminium phosphine class title complex more fully solution join, and then improve the yield of trimethyl aluminium.
According to method of the present invention, wherein, in order to improve the purity of obtained trimethyl aluminium further, preferably, the method also comprises: step (3) solution is joined the trimethyl aluminium obtained and carries out rectifying.Wherein, the condition of the purifying trimethyl aluminium that the condition of described rectifying can be conventional, such as can comprise: temperature is 125-130 DEG C, pressure is normal pressure.
Embodiment
The yield calculation formula of trimethyl aluminium is: yield=M [Al (CH 3) 3] 3*142/M (CH 3i) * 72.
Embodiment 1
The present embodiment is for illustration of the preparation method of trimethyl aluminium of the present invention.
(1) in the reactor being full of nitrogen gas, 570g magnalium Al is added xmg y(x=0.53, y=0.47, x, y are massfraction), 4000g2-methyltetrahydrofuran, 4260g methyl iodide (rate of addition is 3ml/min) is dripped lentamente under agitation in the 2-methyltetrahydrofuran containing magnalium, controlling temperature of reaction is 40 DEG C, when the temperature of question response liquid no longer raises, illustrate that contact reacts reaches terminal (reaction times is 6h), then continue to be warming up to 90 DEG C and steam 2-methyltetrahydrofuran, distill out trimethyl aluminium ethers title complex at 0.01MPa, at 90 DEG C;
(2) the trimethyl aluminium ethers title complex above-mentioned distillation obtained is transferred to the solution filling 2623g triphenylphosphine and joins in still, at 90 DEG C, react 2h, then by reaction solution 90 DEG C, carry out distilling out lower-boiling impurity and remaining 2-methyltetrahydrofuran under 0.01MPa;
(3) temperature be 130 DEG C, under pressure is 0.005MPa, trimethyl aluminium triphenylphosphine complex solution step (2) obtained joins 12h, obtain trimethyl aluminium crude product, by this crude product 125 DEG C, rectifying under normal pressure, obtain 663g trimethyl aluminium product, the yield of this trimethyl aluminium product is 92%, and purity is 99.9999%.
Embodiment 2
The present embodiment is for illustration of the preparation method of trimethyl aluminium of the present invention.
(1) in the reactor being full of nitrogen gas, 1000g magnalium Al is added xmg y(x=0.59, y=0.41, x, y are massfraction), 5000g2-methyltetrahydrofuran, 8520g methyl iodide (rate of addition is 4ml/min) is dripped lentamente under agitation in the 2-methyltetrahydrofuran containing magnalium, controlling temperature of reaction is 50 DEG C, when the temperature of question response liquid no longer raises, illustrate that contact reacts reaches terminal (reaction times is 4h), then continue to be warming up to 90 DEG C and steam 2-methyltetrahydrofuran, distill out trimethyl aluminium ethers title complex at 0.005MPa, at 90 DEG C;
(2) the trimethyl aluminium ethers title complex above-mentioned distillation obtained is transferred to the solution filling 5246g triphenylphosphine and joins in still, at 100 DEG C, react 2h, then by reaction solution 100 DEG C, carry out distilling out lower-boiling impurity and remaining 2-methyltetrahydrofuran under 0.02MPa;
(3) temperature be 155 DEG C, under pressure is 0.01MPa, trimethyl aluminium triphenylphosphine complex solution step (2) obtained joins 12h, obtain trimethyl aluminium crude product, by this crude product 125 DEG C, rectifying under normal pressure, obtain 1268g trimethyl aluminium product, the yield of this trimethyl aluminium product is 88%, and purity is 99.9999%.
Embodiment 3
The present embodiment is for illustration of the preparation method of trimethyl aluminium of the present invention.
(1) in the reactor being full of nitrogen gas, 2000g magnalium Al is added xmg y(x=0.60, y=0.4, x, y are massfraction), 8000g2-methyltetrahydrofuran, 17040g methyl iodide (rate of addition is 5ml/min) is dripped lentamente under agitation in the 2-methyltetrahydrofuran containing magnalium, controlling temperature of reaction is 75 DEG C, when the temperature of question response liquid no longer raises, illustrate that contact reacts reaches terminal (reaction times is 3h), then continue to be warming up to 90 DEG C and steam 2-methyltetrahydrofuran, 0MPa, at 90 DEG C under distill out trimethyl aluminium ethers title complex;
(2) the trimethyl aluminium ethers title complex above-mentioned distillation obtained is transferred to the solution filling 10492g triphenylphosphine and joins in still, at 100 DEG C, react 2h, then by reaction solution 105 DEG C, carry out distilling out lower-boiling impurity and remaining 2-methyltetrahydrofuran under 0.005MPa;
(3) temperature be 180 DEG C, under pressure is 0.01MPa, trimethyl aluminium triphenylphosphine complex solution step (2) obtained joins 5h, obtain trimethyl aluminium crude product, by this crude product 125 DEG C, rectifying under normal pressure, obtain 2592g trimethyl aluminium product, the yield of this trimethyl aluminium product is 90%, and purity is 99.9999%.
Embodiment 4
The present embodiment is for illustration of the preparation method of trimethyl aluminium of the present invention.
Trimethyl aluminium is prepared according to the method for embodiment 1, unlike, by the monobromethane of the amounts such as methyl iodide replaces with, obtain 590g trimethyl aluminium product, the yield of this trimethyl aluminium product is 82%, and purity is 99.9999%.
Embodiment 5
The present embodiment is for illustration of the preparation method of trimethyl aluminium of the present invention.
Trimethyl aluminium is prepared according to the method for embodiment 1, unlike, the temperature of reaction of step (1) controlled to be 20 DEG C, the time is 2h, obtains 576g trimethyl aluminium product, and the yield of this trimethyl aluminium product is 80%, and purity is 99.9999%.。
Embodiment 6
The present embodiment is for illustration of the preparation method of trimethyl aluminium of the present invention.
Trimethyl aluminium is prepared according to the method for embodiment 1, unlike, it is 120 DEG C that solution joins temperature, and pressure is 0.02MPa, and the time is 15h, obtains 619g trimethyl aluminium product, and the yield of this trimethyl aluminium product is 86%, and purity is 99.9999%.
Embodiment 7
The present embodiment is for illustration of the preparation method of trimethyl aluminium of the present invention.
Trimethyl aluminium is prepared according to the method for embodiment 1, unlike, by the diphenylphosphine of the amounts such as triphenylphosphine replaces with, obtain 576g trimethyl aluminium product, the yield of this trimethyl aluminium product is 80%, and purity is 99.9999%.
Comparative example 1
Trimethyl aluminium is prepared according to the method for embodiment 1, unlike, by the methyl chloride of the amounts such as methyl iodide replaces with, obtain 302g trimethyl aluminium product, the yield of this trimethyl aluminium product is 42%, and purity is 99.9999%.
Preparation method of the present invention can significantly improve yield and the purity of trimethyl aluminium, its yield can be made up to more than 80%, high purity 99.9999%, and, the present invention's reactor used can be used as evaporating kettle and uses, simplify technique and equipment, reaction process is easy to control, product also comparatively easy and raw material, the separation of by-products of preparation, be highly suitable for suitability for industrialized production, in addition, its by product can be used for synthesizing Tai-Ace S 150, and almost no waste mine produces.
Embodiment 1 is compared can find out with embodiment 4, when described haloalkane is methyl iodide, the yield of trimethyl aluminium can be improved further, and byproduct of reaction more easily reclaims.
Embodiment 1 is compared can be found out with embodiment 5, and in step (1), contact reacts condition comprises: temperature is 35-75 DEG C, when the time is 3-6h, can improve the yield that can improve trimethyl aluminium further further.
Embodiment 1 is compared can find out with embodiment 6, the solution condition of joining comprises: temperature is 130-180 DEG C, and pressure is 0-0.01MPa, and the time is 5-12h, can make trimethyl aluminium Complexes and/or trimethyl aluminium phosphine class title complex more fully solution join, and then improve the yield of trimethyl aluminium.
Embodiment 1 is compared can find out with embodiment 7, when adopting triphenylphosphine in step (2), yield and the purity of trimethyl aluminium can be improved further.
More than describe the preferred embodiment of the present invention in detail; but the present invention is not limited to the detail in above-mentioned embodiment, within the scope of technical conceive of the present invention; can carry out multiple simple variant to technical scheme of the present invention, these simple variant all belong to protection scope of the present invention.
It should be noted that in addition, each concrete technical characteristic described in above-mentioned embodiment, in reconcilable situation, can be combined by any suitable mode, in order to avoid unnecessary repetition, the present invention illustrates no longer separately to various possible array mode.
In addition, also can carry out arbitrary combination between various different embodiment of the present invention, as long as it is without prejudice to thought of the present invention, it should be considered as content disclosed in this invention equally.
Claims (10)
Hide Dependent
1. a preparation method for trimethyl aluminium, is characterized in that, the method comprises:
(1) exist at ether solvent and under inert atmosphere, by magnalium and haloalkane contact reacts, obtain trimethyl aluminium ethers title complex;
(2) by trimethyl aluminium ethers title complex and high boiling amine and/or phosphines contact reacts, trimethyl aluminium Complexes and/or trimethyl aluminium phosphine class title complex is obtained;
(3) title complex that step (2) obtains is carried out solution to join.
2. method according to claim 1, wherein, described haloalkane is methyl iodide and/or monobromethane, is preferably methyl iodide.
3. method according to claim 1, wherein, described ether solvent is alkyl oxide, is preferably at least one in ether, tetrahydrofuran (THF) and methyltetrahydrofuran.
4. method according to claim 1, wherein, described aminated compounds is at least one in pentanoic, Tributylamine and trioctylamine; Described phosphines is at least one in triphenylphosphine, diphenylphosphine.
5. method according to claim 1, wherein, described magnalium is Al xmg y, wherein x=0.4-0.6, y=0.6-0.4, x+y=1, x, y are massfraction.
6. method according to claim 1, wherein, in step (1), in magnalium, the mol ratio of aluminium and haloalkane is 1:2-12, is preferably 1:2.5-9.
7. method according to claim 1, wherein, in step (2), relative to 1mol haloalkane, the consumption of amine and/or phosphines is 0.3-0.8mol.
8. method according to claim 1, wherein, in step (1), contact reacts condition comprises: temperature is 20-90 DEG C, and the time is 2-8h, and preferably, temperature is 35-75 DEG C, and the time is 3-6h.
9. method according to claim 1, wherein, in step (3), the solution condition of joining comprises: temperature is 120-200 DEG C, and pressure is 0-0.03MPa, and the time is 5-15h, and being preferably temperature is 130-180 DEG C, and pressure is 0-0.01MPa, and the time is 5-12h.
10. method according to claim 1, wherein, the method also comprises: step (3) solution is joined the trimethyl aluminium obtained and carries out rectifying[7]
Applications
[edit]Catalysis
[edit]Starting with the invention of Ziegler-Natta catalysis, organoaluminium compounds have a prominent role in the production of polyolefins, such as polyethylene and polypropylene. Methylaluminoxane, which is produced from TMA, is an activator for many transition metal catalysts.
Semiconductor applications
[edit]TMA is also used in semiconductor fabrication to deposit thin film, high-k dielectrics such as Al2O3 via the processes of chemical vapor deposition or atomic layer deposition. TMA is the preferred precursor for metalorganic vapour phase epitaxy (MOVPE) of aluminium-containing compound semiconductors, such as AlAs, AlN, AlP, AlSb, AlGaAs, AlInGaAs, AlInGaP, AlGaN, AlInGaN, AlInGaNP, etc. Criteria for TMA quality focus on (a) elemental impurities, (b) oxygenated and organic impurities.
Photovoltaic applications
[edit]In deposition processes very similar to semiconductor processing, TMA is used to deposit thin film, low-k (non-absorbing) dielectric layer stacks with Al2O3 via the processes of chemical vapor deposition or atomic layer deposition. The Al2O3 provides excellent surface passivation of p-doped silicon surfaces. The Al2O3 layer is typically the bottom layer with multiple silicon nitride (SixNy) layers for capping.
Reactions
[edit]Hydrolysis and related protonolysis reactions
[edit]Trimethylaluminium is hydrolyzed readily, even dangerously:
- Al2Me6 + 3 H2O → Al2O3 + 6 CH4
Under controlled conditions, the reaction can be stopped to give methylaluminoxane:
- AlMe3 + H2O → 1/n [AlMeO]n + 2 CH4
Alcoholysis and aminolysis reactions proceed comparably. For example, dimethylamine gives the dialuminium diamide dimer:[8]
- 2 AlMe3 + 2 HNMe2 → [AlMe2NMe2]2 + 2 CH4
Reactions with metal chlorides
[edit]TMA reacts with many metal halides to install alkyl groups. When combined with gallium trichloride, it gives trimethylgallium.[9] Al2Me6 reacts with aluminium trichloride to give (AlMe2Cl)2.
TMA/metal halide reactions have emerged as reagents in organic synthesis. Tebbe's reagent, which is used for the methylenation of esters and ketones, is prepared from TMA and titanocene dichloride.[10] In combination with 20 to 100 mol % Cp2ZrCl2 (zirconocene dichloride), the (CH3)2Al-CH3 adds "across" alkynes to give vinyl aluminium species that are useful in organic synthesis in a reaction known as carboalumination.[11]
Adducts
[edit]As for other "electron-deficient" compounds, trimethylaluminium gives adducts R3N.AlMe3. The Lewis acid properties of AlMe3 have been quantified.[12] The enthalpy data show that AlMe3 is a hard acid and its acid parameters in the ECW model are EA =8.66 and CA = 3.68.
These adducts, e.g. the complex with the tertiary amine DABCO, are safer to handle than TMA itself.[13]
The NASA ATREX mission (Anomalous Transport Rocket Experiment) employed the white smoke that TMA forms on air contact to study the high altitude jet stream.
Synthetic reagent
[edit]TMA is a source of methyl nucleophiles, akin to methyl lithium, but less reactive. It reacts with ketones to give, after a hydrolytic workup, tertiary alcohols.
Safety
[edit]Trimethylaluminium is pyrophoric, reacting violently with air and water.
References
[edit]- ^ a b c d e f Sigma-Aldrich Co., Trimethylaluminum. Retrieved on 2014-05-05.
- ^ a b c d e "Trimethyl aluminum".
- ^ Krause, Michael J.; Orlandi, Frank; Saurage, Alfred T.; Zietz, Joseph R. (2000). "Aluminum Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_543. ISBN 978-3527306732.
- ^ C. Elschenbroich (2006). Organometallics. VCH. ISBN 978-3-527-29390-2.
- ^ Holleman, A. F.; Wiberg, E. (2001). Inorganic Chemistry. San Diego: Academic Press. ISBN 0-12-352651-5.
- ^ Vass, Gábor; Tarczay, György; Magyarfalvi, Gábor; Bödi, András; Szepes, László (2002). "HeI Photoelectron Spectroscopy of Trialkylaluminium and Dialkylaluminium Hydride Compounds and Their Oligomers". Organometallics. 21 (13): 2751–2757. doi:10.1021/om010994h.
- ^ https://patents.google.com/patent/CN105175440A/en
- ^ Lipton, Michael F.; Basha, Anwer; Weinreb, Steven M. (1979). "Conversion of Esters to Amides with Dimethylaluminium Amides: N,N-Dimethylcyclohexanecarboxamide". Organic Syntheses. 59: 49. doi:10.15227/orgsyn.059.0049.
- ^ Gaines, D. F.; Borlin, Jorjan; Fody, E. P. (1974). "Trimethylgallium". Inorganic Syntheses. Vol. 15. pp. 203–207. doi:10.1002/9780470132463.ch45. ISBN 978-0-470-13246-3.
- ^ Pine, S. H.; Kim, V.; Lee, V. (1990). "Enol ethers by methylenation of esters: 1-Phenoxy-1-phenylethene and 3,4-dihydro-2-methylene-2H-1-benzopyran". Org. Synth. 69: 72. doi:10.15227/orgsyn.069.0072.
- ^ Negishi, E.; Matsushita, H. (1984). "Palladium-Catalyzed Synthesis of 1,4-Dienes by Allylation of Alkenyalane: α-Farnesene [1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-]". Organic Syntheses. 62: 31. doi:10.15227/orgsyn.062.0031.
- ^ Henrickson, C. H.; Duffy, D.; Eyman, D. P. (1968). "Lewis acidity of Alanes. Interactions of Trimethylalane with Amines, Ethers, and Phosphines". Inorganic Chemistry. 7 (6): 1047–1051. doi:10.1021/ic50064a001.
- ^ Vinogradov, Andrej; Woodward, S. (2010). "Palladium-Catalyzed Cross-Coupling Using an Air-Stable Trimethylaluminium Source. Preparation of Ethyl 4-Methylbenzoate". Organic Syntheses. 87: 104. doi:10.15227/orgsyn.087.0104.
External links
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