lithium dimethylamide | 3585-33-9

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: lithium dimethylamide
• 英文别名: lithium dimethylamine；dimethylamine lithium；lithium;dimethylazanide
• CAS: 3585-33-9
• 化学式: C₂H₆LiN
• 分子量: 51.0173
• InChiKey: YDGSUPBDGKOGQT-UHFFFAOYSA-N

物化性质

• 沸点：
  68-70 °C
• 密度：
  0.68 g/mL at 25 °C
• 闪点：
  -23 °C
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  -2.38
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  4.2
• 危险品标志：
  F,C,N
• 安全说明：
  S16,S26,S27,S29,S33,S36/37/39,S45,S62,S9
• 危险类别码：
  R67,R17,R11,R51/53,R62,R34,R65,R48/20
• 海关编码：
  2924199090
• 危险类别：
  4.2
• 危险品运输编号：
  UN 3394 4.2/PG 1
• 危险标志：
  GHS02,GHS05,GHS07,GHS08,GHS09
• 危险性描述：
  H225,H250,H261,H304,H314,H336,H361f,H373,H411
• 危险性防范说明：
  P210,P231 + P232,P280,P301 + P310,P302 + P334,P303 + P361 + P353,P304 + P340 + P310,P305 + P351 + P338,P331,P422
• 储存条件：
  请将产品存放在避光、通风干燥的地方，并密封保存。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Lithium dimethylamide
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 3585-33-9

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Pyrophoric solids (Category 1), H250
Substances, which in contact with water, emit flammable gases (Category 2), H261
Skin corrosion (Category 1B), H314
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
F, C Highly flammable, Corrosive R17, R34
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
Catches fire spontaneously if exposed to air.
In contact with water releases flammable gases.
Causes severe skin burns and eye damage.
Precautionary statement(s)
Do not allow contact with air.
P231 + P232 Handle under inert gas. Protect from moisture.
Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Immediately call a POISON CENTER or doctor/ physician.
Store contents under inert gas.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C2H6LiN
Molecular Weight : 51,02 g/mol
CAS-No. : 3585-33-9
EC-No. : 222-714-3
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Lithium dimethylamide
CAS-No. 3585-33-9 Pyr. Sol. 1; Water-react. 2; <= 100 %
EC-No. 222-714-3 Skin Corr. 1B; H250, H261,
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Lithium dimethylamide
CAS-No. 3585-33-9 F, C, R17 - R34 <= 100 %
EC-No. 222-714-3
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Take off contaminated clothing and shoes immediately. Wash off with soap and plenty of water. Consult a
physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Dry powder Carbon dioxide (CO2)
Unsuitable extinguishing media
Water
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Lithium oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Contain spillage, and then collect with an electrically protected vacuum cleaner or
by wet-brushing and place in container for disposal according to local regulations (see section 13). Do
not flush with water. Keep in suitable, closed containers for disposal. Contain spillage, pick up with an
electrically protected vacuum cleaner or by wet-brushing and transfer to a container for disposal
according to local regulations (see section 13).
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Keep away from sources of ignition
- No smoking.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Never allow product to get in contact with water during storage.
Handle and store under inert gas. Moisture sensitive.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands. Protective gloves against thermal risks
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, Flame retardant antistatic protective clothing, The type
of protective equipment must be selected according to the concentration and amount of the
dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
Reacts violently with water.
Conditions to avoid
Exposure to moisture.
Incompatible materials
Strong oxidizing agents, acids
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and
skin., Cough, Shortness of breath, Headache, Nausea

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal
company. Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 3393 IMDG: 3393 IATA: 3393
UN proper shipping name
ADR/RID: ORGANOMETALLIC SUBSTANCE, SOLID, PYROPHORIC, WATER-REACTIVE (Lithium
dimethylamide)
IMDG: ORGANOMETALLIC SUBSTANCE, SOLID, PYROPHORIC, WATER-REACTIVE (Lithium
dimethylamide)
IATA: Organometallic substance, solid, pyrophoric, water-reactive (Lithium dimethylamide)
Passenger Aircraft: Not permitted for transport
Cargo Aircraft: Not permitted for transport
Transport hazard class(es)
ADR/RID: 4.2 (4.3) IMDG: 4.2 (4.3) IATA: 4.2 (4.3)
Packaging group
ADR/RID: I IMDG: I IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  lithium dimethylamide 以 gaseous matrix 为溶剂， 生成 N-甲基甲亚胺
  参考文献：
  名称：

  Withnall, Robert; Dunkin, Ian R.; Snaith, Ronald, Journal of the Chemical Society. Perkin transactions II, 1994, # 9, p. 1973 - 1978

  摘要：

  DOI：
• 作为产物：
  描述：

  二甲胺 在 正丁基锂 作用下， 以 hexanes 为溶剂， 生成 lithium dimethylamide
  参考文献：
  名称：

  新型铬（ii）和铬（iii）杂蝎子配合物的合成和乙烯三聚化能力†

  摘要：

  的反应 （Me 2 pz）2 CHSiMe 2 N（H）R（R = i Pr或Ph）或（Me 2 pz）2 CHSiMe 2 NMe 2 和 CrCl 3（四氢呋喃）3 或者 氯化铬2（THF）2得到Cr {（Me 2 pz）2 CHSiMe 2 NR 1 R 2 } Cl 3（R 1 =H，R 2 =我镨（10）或Ph（11）；R 1 = R 2 = Me（15））或Cr {（Me 2 pz）2 CHSiMe 2 NR 1 R 2 } Cl 2（THF）（R 1 =H，R 2 =我镨（12）或Ph（13）；R 1＝ R 2＝ Me（16））。对化合物10和11进行了晶体学表征，并使用SQUID磁力分析法评估了所有新化合物的磁行为。的反应CrCl 3（四氢呋喃）3 和 Li {C（Me 2 pz）3 }（THF） 给出了两性离子复合物 Cr {C（Me 2 pz）3 } Cl 2（THF）

  DOI：

  10.1039/b926333k
• 作为试剂：
  描述：

  2-bromo-4-phenylbutane 、 B-cyclobutyl-9-borabicyclo[3.3.1]nonane 在 lithium dimethylamide 、 C₃₃H₃₉Cl₂F₄FeLiN₂O₂ 作用下， 以 苯 为溶剂， 以20 mg的产率得到(3-cyclobutylbutyl)benzene
  参考文献：
  名称：

  合理设计的用于 C(sp3)−C(sp2) 和 C(sp3)−C(sp3) Suzuki-Miyaura 交叉偶联的铁 (II) 催化剂

  摘要：

  描述了一种明确的铁催化剂，具有高效率，适用于涉及 C(sp 3 ) 伴侣的 Suzuki-Miyaura 偶联。在氨基锂碱存在下，该催化剂首次实现了 1°、2° 和 3° 卤代烷与（杂）芳基硼酸酯的 C(sp 3 )−C(sp 2 ) 偶联：以及在温和条件下和具有广泛官能团耐受性的 1° 和 2° 烷基卤化物与 1° 和 2° 烷基硼烷的 C(sp 3 )−C(sp 3 ) 偶联。

  DOI：

  10.1002/anie.202408419

文献信息

• Bestimmung der ionenpaar-basizitǎt von lithium- und kaliumamiden
  作者：Hubertus Ahlbrecht、Gunther Scheneider

  DOI：10.1016/s0040-4020(01)82054-8

  日期：1986.1

  Ion pair basicities of lithio and potassio salts of some secondary amines were determined by equilibration with benzyl compounds. With these bases it is possible to span a range of about 19 pK-units from pK = 27 up to 46. The structural dependence of thermodynamic as well as kinetic basicity is discussed. Some new effective amide bases for preparative purposes are recommended. For the first time the

  通过与苄基化合物平衡来确定某些仲胺的硫代和钾代盐的离子对碱性。有了这些基础，就有可能跨越从pK = 27到46的约19 pK单位范围。讨论了热力学以及动力学基础的结构依赖性。推荐用于制备目的的一些新的有效酰胺碱。甲苯的pK值首次通过直接平衡确定。在四氢呋喃中为40.7。
• Mononuclear Tantalum(IV, d¹) Imido Complexes Supported by the Monocyclopentadienyl, Amidinate and Guanidinate Ligand Sets As Models to Explore Dinitrogen Fixation by “End-On-Bridged” Dinuclear {[Ta(IV, d¹)]}₂(μ-η¹:η¹-N₂) Complexes
  作者：Brendan L. Yonke、Andrew J. Keane、Peter Y. Zavalij、Lawrence R. Sita

  DOI：10.1021/om200961r

  日期：2012.1.9

  Two independent synthetic routes to the monocyclopentadienyl, amidinate (CpAm) and guanidinate (CpGu) mononuclear Ta(IV, d1) terminal imido complexes Cp*Ta[N(iPr)C(X)N(iPr)][N(tBu)] (Cp* = η5-C5Me5) for X = Me (1) and NMe2 (2), respectively, were developed. For 1, synthesis proceeded via the amido, chloride intermediate Cp*Ta[N(iPr)C(Me)N(iPr)](Cl)[NH(tBu)] (4), which was kinetically deprotonated with

  到单环戊二烯基，a酸酯（CpAm）和胍基（CpGu）单核Ta（IV，d 1）末端亚氨基配合物Cp * Ta [N（i Pr）C（X）N（i Pr）] [N（吨丁基）]（CP * =η 5 -C 5我5）为X =我（1）和NME 2（2），分别开发的。对于1，合成是通过酰胺基氯化物中间体Cp * Ta [N（i Pr）C（Me）N（i Pr）]（Cl）[NH（t Bu）]（4）进行的，该反应用LiN进行了动力学去质子化。 （我Pr）2得到酰胺基，酰胺基物种Cp * Ta [N（i Pr）C（CH 2）N（i Pr）[NH（t Bu）]（5）。在甲苯溶液中，5进行定量互变异构化成所需的CpAm末端亚氨基1。对于2，首先合成了酰胺氯化物中间体Cp * Ta [N（i Pr）C（NMe 2）N（i Pr）]（Cl）[NH（t Bu）]（8），然后与TEMPO反应生成提供Ta（V）酰亚胺氯化物Cp *
• Scandium and yttrium complexes of the diamide–diamine donor ligand (2-C5H4N)CH2N(CH2CH2NSiMe3)2: chloride, primary and secondary amide, benzamidinate and alkyl functionalised derivatives
  作者：Michael E. G. Skinner、Philip Mountford

  DOI：10.1039/b111469g

  日期：2002.4.9

  Five- and six-coordinate scandium and yttrium complexes of the recently described diamide–diamine donor ligand N2NN′ (where H2N2NN′ = (2-C5H4N)CH2NCH2CH2N(H)SiMe3}2) are described. Reaction of ScCl3 with Li2N2NN′ gave five-coordinate [ScCl(N2NN′)] 1 in excellent yield. The corresponding reaction with YCl3 in tetrahydrofuran (thf) or pyridine (py) solution afforded “ate” complexes best described as [YCl(N2NN′)(L)]·1.5(LiCl) (L = thf 2 or py 3). The two chloride complexes 1 and 2 are useful starting materials for primary and secondary amide, benzamidinate and alkyl complexes of Sc and Y supported by the N2NN′ ligand. Thus reaction of 1 or 2 with LiN(SiMe3)2·Et2O, LiNMe2 or LiNHR (R = tBu or Ar, where Ar = 2,6-C6H3iPr2) gave the corresponding five-coordinate amide derivatives [M(NRR″)(N2NN′)] (M = Sc, R = R″ = SiMe34 or Me 6, or R = H, R″ = tBu 8 or Ar 9; M = Y, R = R″ = SiMe35, or R = H, R″ = Ar 10). The crystal structure of 5 is described. The σ-bond metathesis reaction of [Sc(NMe2)(N2NN′)] 6 with ArFNH2 (ArF = C6F5) gave the corresponding primary flurophenylamide derivative 7. The reaction of 1 or 2 with Li[PhC(NSiMe3)2] gave the fluxional, six-coordinate benzamidinate derivatives [MPhC(NSiMe3)2}(N2NN′)] (M = Sc 11 or Y 12), the crystal structures of which are reported. Finally, reaction of 1 with LiCH2SiMe3 formed the alkyl derivative [Sc(CH2SiMe3)(N2NN′)] 13 in reasonable yield; the crystal structure of 13 is described.

  最近报道的二酰胺-二胺供体配体N2NN'（其中H2N2NN' = (2-C5H4N)CH2NCH2CH2N(H)SiMe3}2）的五配位和六配位钪和钇配合物。将ScCl3与Li2N2NN'反应得到了高产率的五配位[ScCl(N2NN')] 1。在四氢呋喃（thf）或吡啶（py）溶液中，将YCl3与Li2N2NN'反应得到了最佳描述为[YCl(N2NN')(L)]·1.5(LiCl)的“ate”配合物（L = thf 2或py 3）。两种氯配合物1和2是制备由N2NN'配体支撑的Sc和Y的一级和二级酰胺、苯甲酰亚胺和烷基配合物的重要起始材料。因此，将1或2与LiN(SiMe3)2·Et2O、LiNMe2或LiNHR（R = tBu或Ar，其中Ar = 2,6-C6H3iPr2）反应得到了相应的五配位酰胺衍生物[M(NRR')(N2NN')]（M = Sc，R = R' = SiMe34或Me 6，或R = H，R' = tBu 8或Ar 9；M = Y，R = R' = SiMe35，或R = H，R' = Ar 10）。描述了5的晶体结构。[Sc(NMe2)(N2NN')] 6与ArFNH2（ArF = C6F5）的σ-键置换反应得到了相应的一级氟苯甲酰胺衍生物7。将1或2与Li[PhC(NSiMe3)2]反应得到了动态的六配位苯甲酰亚胺衍生物[MPhC(NSiMe3)2}(N2NN')]（M = Sc 11或Y 12），报告了其晶体结构。最后，将1与LiCH2SiMe3反应形成了合理的产率的烷基衍生物[Sc(CH2SiMe3)(N2NN')] 13；描述了13的晶体结构。
• Acyclische isomere von aminofluorsilanen, intramolekulare cyclisierung
  作者：Uwe Klingebiel

  DOI：10.1016/s0022-328x(00)81268-1

  日期：1978.5

  Fluorosilanes react with lithiated amines to yield aminofluorosilanes. Iso- and sec-butylaminofluorosilanes with bulky ligands form the isomers (I–VII). The cyclisation of monoorganofluorosilanes depends on the size of the substituents. IV and V dimerise by HF-elimination (VIII, IX) and VII cyclises by migration of a methanide ion (X). The mass, 1H, 19F and 29Si NMR spectra of the compounds are reported

  氟硅烷与锂化胺反应生成氨基氟硅烷。具有庞大配体的异丁基和仲丁基氨基氟硅烷形成异构体（I–VII）。单有机氟硅烷的环化取决于取代基的大小。IV和V通过HF消除（VIII，IX）进行二聚，而VII通过甲烷离子（X）的迁移环化。报告了化合物的质量，1 H，19 F和29 Si NMR光谱。
• Reactivity of a Titanium Dinitrogen Complex Supported by Guanidinate Ligands:  Investigation of Solution Behavior and a Novel Rearrangement of Guanidinate Ligands
  作者：Sarah M. Mullins、Andrew P. Duncan、Robert G. Bergman、John Arnold

  DOI：10.1021/ic010631+

  日期：2001.12.1

  rotation and racemization reactions were observed. Rearrangement of the guanidinate ligand to an asymmetrical bonding mode utilizing the dimethylamino and amide-nitrogen atoms is observed in the bridging oxo and sulfido derivatives (4 and 5). These compounds are formed by the reactions of 2 with pyridine N-oxide and propylene sulfide, respectively. The ligand rearrangement was observed to be reversible

  钛二氮配合物[[（Me（2）N）C（N（i）Pr）（2）]（2）Ti]（2）（N（2））（2）通过还原二氯化物前体，[（Me（2）N）C（N（i）Pr）（2）]（2）TiCl（2）（1）。二氮配合物与叠氮化苯反应生成钛亚氨基配合物[[Me（2）N）C（N（i）Pr）（2）]（2）TiNPh（3）。使用可变温度和二维NMR技术研究了化合物1-3中胍基配体的流动行为。观察到胍基配体旋转和消旋反应。在桥联的羰基和硫代衍生物（4和5）中，利用二甲基氨基和酰胺氮原子将胍盐配体重排为不对称键合模式。这些化合物分别由2与吡啶N-氧化物和硫化丙烯的反应形成。对于桥连的硫基络合物5，观察到配体重排是可逆的。该化合物的结构对温度和溶剂敏感。讨论了化合物1-5的固态和溶液结构。