仲丁基锂

仲丁基锂
	IUPAC名; sec-Butyllithium
	系统名; Butan-2-yllithium
英文名	sec-Butyllithium
识别
CAS号	598-30-1
PubChem	102446
ChemSpider	10254345
SMILES	[Li]C(C)CC;
InChI	1/C4H9.Li/c1-3-4-2;/h3H,4H2,1-2H3;/rC4H9Li/c1-3-4(2)5/h4H,3H2,1-2H3;
InChIKey	VATDYQWILMGLEW-MHILWDCKAX
Beilstein	3587206
EINECS	209-927-7
性质
化学式	C4H9Li
摩尔质量	64.06 g·mol−1
外观	无色液体
沸点	90℃ (0.05 Torr)
溶解性	可溶于环己烷
pKa	51
相关物质
相关化学品	正丁基锂; 叔丁基锂
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

仲丁基锂，化学式 CH
3CHLiCH
2CH
3，简称sec-BuLi或s-BuLi，是一种有机锂化合物，为正丁基锂和叔丁基锂的异构体。这种有手性的有机锂试剂是有机合成中仲丁基碳阴离子的来源。^[2]

Quick Facts 仲丁基锂, 识别 ...

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制备

仲丁基锂可以由2-氯丁烷和单质锂反应而成。^[4]

性质

物理性质

仲丁基锂是一种无色粘稠液体。^[5]通过质谱法，发现了仲丁基锂的四聚体结构。^[6]在苯、环己烷和环戊烷等非极性溶剂中，它就是以四聚体存在的。^[5]^[7]^[8]在 −41 °C的环戊烷溶液中使用⁶Li-NMR，可以探测到六聚体。^[8]在具有配体性质的溶剂（如四氢呋喃）里，二聚体和单体之间存在平衡。^[9]

化学性质

相较于正丁基锂，仲丁基锂在室温下和乙醚、THF的反应更快。它会分解成氢化锂和各种丁烯（1-丁烯、顺式和反式的2-丁烯）^[10]^[11]

仲丁基锂可自燃^[1]，并产生红色的火焰。

用处

碳-锂键是高度极性的，所以其中的碳原子的亲核性和碱性很强。位阻更多的仲丁基锂的碱性比正丁基锂还强。这些性质可用于各种用途。举个例子，当有机化合物的C-H键酸性（德语：C-H-Acidität）很弱，正丁基锂不能使用时，可以使用仲丁基锂。它也用于催化异戊二烯、丁二烯和苯乙烯的聚合反应。^[1]

参考资料

[1]
Entry on Butyllithium. at: Römpp Online. Georg Thieme Verlag, retrieved 2013-12-06.
[2]
Ovaska, T. V. "s-Butyllithium" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons: New York. doi:10.1002/047084289X.rb397.
[3]
来源：Sigma-Aldrich Co., product no. 195596 （2011-04-23查阅）.
[4]
H. Gilman, F. W. Moore, O. Baine: Secondary and Tertiary Alkyllithium Compounds and Some Interconversion Reactions with Them. In: J. Am. Chem. Soc. 63, 1941, S. 2479–2482, doi:10.1021/ja01854a046.
[5]
U. Wietelmann, R. J. Bauer: Lithium and Lithium Compounds. In: Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag, Weinheim 2005, doi:10.1002/14356007.a15_393
[6]
D. Plavsic, D. Srzic, L. Klasinc: Mass spectrometric investigations of alkyllithium compounds in the gas phase. In: J. Phys. Chem. 90, 1986, S. 2075–2080, doi:10.1021/j100401a020.
[7]
S. Bywater, D. J. Worsfold: Alkyllithium anionic polymerization initiators in hydrocarbon solvents. In: J. Organomet. Chem. 10, 1967, S. 1–6.
[8]
G. Fraenkel, M. Henrichs, M. Hewitt, B. M. Su: Structure and dynamic behavior of a chiral alkyllithium compound: ¹³C and ⁶Li NMR of sec-butyllithium. In: J. Am. Chem. Soc. 106, 1984, S. 255–256.
[9]
W. Bauer, W. R. Winchester, P. von Schleyer: Monomeric organolithium compounds in tetrahydrofuran: tert-butyllithium, sec-butyllithium, supermesityllithium, mesityllithium, and phenyllithium. Carbon-lithium coupling constants and the nature of carbon-lithium bonding. In: Organometallics. 6, 1987, S. 2371–2379, doi:10.1021/om00154a017.
[10]
W. H. Glaze, J. Lin, E. G. Felton: The Thermal Decomposition of sec.-Butyllithium. In: J. Org. Chem. 30, 1965, S. 1258–1259, doi:10.1021/jo01015a514.
[11]
W. H. Glaze, J. Lin, E. G. Felton: The Pyrolysis of Unsolvated Alkyllithium Compounds. In: J. Org. Chem. 31, 1966, S. 2643–2645, doi:10.1021/jo01346a044.

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扩展阅读

Heinz G. O. Becker u. a.: Organikum. 21. Auflage. Wiley-VCH, Weinheim 2001, ISBN 3-527-29985-8.
Christoph Elschenbroich: Organometallchemie. 5. Auflage. Teubner, Wiesbaden 2005, ISBN 3-519-53501-7.

[roempp-1] [1]
Entry on Butyllithium. at: Römpp Online. Georg Thieme Verlag, retrieved 2013-12-06.

[Ovaska-2] [2]
Ovaska, T. V. "s-Butyllithium" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons: New York. doi:10.1002/047084289X.rb397.

[Sigma-3] [3]
来源：Sigma-Aldrich Co., product no. 195596 （2011-04-23查阅）.

[4] [4]
H. Gilman, F. W. Moore, O. Baine: Secondary and Tertiary Alkyllithium Compounds and Some Interconversion Reactions with Them. In: J. Am. Chem. Soc. 63, 1941, S. 2479–2482, doi:10.1021/ja01854a046.

[Ullmann-5] [5]
U. Wietelmann, R. J. Bauer: Lithium and Lithium Compounds. In: Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag, Weinheim 2005, doi:10.1002/14356007.a15_393

[Plavsic-6] [6]
D. Plavsic, D. Srzic, L. Klasinc: Mass spectrometric investigations of alkyllithium compounds in the gas phase. In: J. Phys. Chem. 90, 1986, S. 2075–2080, doi:10.1021/j100401a020.

[7] [7]
S. Bywater, D. J. Worsfold: Alkyllithium anionic polymerization initiators in hydrocarbon solvents. In: J. Organomet. Chem. 10, 1967, S. 1–6.

[Fraenkel-8] [8]
G. Fraenkel, M. Henrichs, M. Hewitt, B. M. Su: Structure and dynamic behavior of a chiral alkyllithium compound: ¹³C and ⁶Li NMR of sec-butyllithium. In: J. Am. Chem. Soc. 106, 1984, S. 255–256.

[Bauer-9] [9]
W. Bauer, W. R. Winchester, P. von Schleyer: Monomeric organolithium compounds in tetrahydrofuran: tert-butyllithium, sec-butyllithium, supermesityllithium, mesityllithium, and phenyllithium. Carbon-lithium coupling constants and the nature of carbon-lithium bonding. In: Organometallics. 6, 1987, S. 2371–2379, doi:10.1021/om00154a017.

[Glaze-10] [10]
W. H. Glaze, J. Lin, E. G. Felton: The Thermal Decomposition of sec.-Butyllithium. In: J. Org. Chem. 30, 1965, S. 1258–1259, doi:10.1021/jo01015a514.

[Glaze2-11] [11]
W. H. Glaze, J. Lin, E. G. Felton: The Pyrolysis of Unsolvated Alkyllithium Compounds. In: J. Org. Chem. 31, 1966, S. 2643–2645, doi:10.1021/jo01346a044.

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