二苯基膦基锂

二苯基膦基锂
别名	二苯基磷化锂
识别
CAS号	4541-02-0
PubChem	3478053
ChemSpider	2719164
SMILES	[Li+].C1=CC=C(C=C1)[P-]C2=CC=CC=C2;
性质
化学式	C12H10LiP
摩尔质量	192.12 g·mol−1
外观	浅黄色固体
溶解性	醚类
危险性
	GHS危险性符号;
GHS提示词	危险
H-术语	H302, H312, H314, H332, H400, H410
P-术语	P260, P261, P264, P270, P271, P273, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

二苯基膦基锂是一种化合物，化学式为(C₆H₅)₂PLi，它是对空气敏感的固体，可用于制备其它含二苯基膦基团的化合物。其乙醚配合物是红色的。

合成

二苯基膦基锂可由二苯基氯化膦、^[2]三苯基膦^[3]^[4]或四苯基二膦被金属钠还原得到：

(C₆H₅)₂PCl + 2 Li → (C₆H₅)₂PLi + LiCl

(C₆H₅)₃P + 2 Li → (C₆H₅)₂PLi + LiC₆H₅

(C₆H₅)₄P₂ + 2 Li → 2 (C₆H₅)₂PLi

它也可由二苯基膦脱氢得到。

反应

二苯基膦基锂可以在水中水解，生成二苯基膦：^[4]

(C₆H₅)₂PLi + H₂O → (C₆H₅)₂PH + LiOH

它和卤代烃反应，生成叔膦：^[5]

(C₆H₅)₂PLi + RX → (C₆H₅)₂PR + LiX

例如，它和1,6-二氯己烷在四氢呋喃中反应，可以得到1,6-双(二苯基膦基)己烷。^[6]

它可用作甲基季铵盐的脱甲基试剂。^[7]它和金属卤化物（或有机金属卤化物^[8]^[9]）反应，生成过渡金属膦配合物。^[10]

参考文献

^ Ruth A. Bartlett, Marilyn M. Olmstead, Philip P. Power. Structural Characterization of the Solvate Complexes of the Lithium Diorganophosphides [{Li(Et₂O)PPh₂}_∞], [{Li(THF)₂PPh₂}_∞], and [{Li(THF)P(C₆H₁₁)₂}_∞]. Inorg. Chem. 1986, 25: 1243–1247. doi:10.1021/ic00228a034.
^ R. Goldsberry Kim Cohn. Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)‐phosphine. Inorganic Syntheses. 1972, 13: 26–32. doi:10.1002/9780470132449.ch7.
^ George W. Luther, III, Gordon Beyerle. Lithium Diphenylphosphide and Diphenyl(Trimethylsilyl)Phosphine. Inorganic Syntheses. 1977, 17: 186–188. doi:10.1002/9780470132487.ch51.
^ ^4.0 ^4.1 V. D. Bianco, S. Doronzo. Diphenylphosphine. Inorganic Syntheses. 1976, 16: 161–188. doi:10.1002/9780470132470.ch43.
^ W. Levason, C. A. Mcauliffe. Cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine. Inorganic Syntheses. 1976, 16: 188–192. doi:10.1002/9780470132470.ch50.
^ Cao, Guangxiu; Ma, Huailing; Li, Guanliang; Li, Jiqin. Study on synthesis of 1,6-bis(diphenylphosphinel)hexane. Huaxue Yanjiu Yu Yingyong, 2006. 18 (12): 1464-1468.
^ Plenat, Francoise; Cahyono, Bambang; Cristau, Henri-Jean. Lithium diphenylphosphide: a new demethylation reagent for methylammonium salts. Comptes Rendus de l'Academie des Sciences, Serie IIb: Mecanique,Physique, Chimie, Astronomie, 1995. 320 (10): 539-543. ISSN: 1251-8069.
^ Alcalde, Maria Isabel; de la Mata, Javier; Gómez, Manuel; Royo, pascual; Sánchez, Fernando. Half-sandwich isocyanide, phosphine, methyl and phosphanido pentamethylcyclopentadienylniobium (V) complexes. Journal of Organometallic Chemistry. 1995, 492 (2): 151–155. ISSN 0022-328X. doi:10.1016/0022-328X(94)05289-N.
^ Cano, Ana; Cuenca, Tomás; Galakhov, Mikhail; Rodríguez, Gema M.; Royo, Pascual; Cardin, Christine J.; Convery, Maire A. Fulvalene titanium and zirconium complexes: synthesis and NMR study of phosphanido-, alkyl-, and alkynyl-derivatives. X-ray crystal structures of [{Ti(η5−C₅H₅)(μ−PPH₂)}₂{μ−(η5−C₅H₄−η5−C₅H₄)}] and [{Zr(η5−C₅H₅)(μ−C≡CSiMe₃)}₂{μ−(η5−C₅H₄−η5−C₅H₄)}]. Journal of Organometallic Chemistry. 1995, 493 (1-2): 17–25. ISSN 0022-328X. doi:10.1016/0022-328X(94)05288-M.
^ Issleib, Kurt; Froehlich, Hans Otto. Alkali metal-phosphorus compounds and their reactive behavior. XIII. Preparation and properties of zinc and cuprous diphenylphosphide. Chemische Berichte, 1962. 95: 375-380. ISSN: 0009-2940.

[1] Ruth A. Bartlett, Marilyn M. Olmstead, Philip P. Power. Structural Characterization of the Solvate Complexes of the Lithium Diorganophosphides [{Li(Et₂O)PPh₂}_∞], [{Li(THF)₂PPh₂}_∞], and [{Li(THF)P(C₆H₁₁)₂}_∞]. Inorg. Chem. 1986, 25: 1243–1247. doi:10.1021/ic00228a034.

[2] R. Goldsberry Kim Cohn. Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)‐phosphine. Inorganic Syntheses. 1972, 13: 26–32. doi:10.1002/9780470132449.ch7.

[3] George W. Luther, III, Gordon Beyerle. Lithium Diphenylphosphide and Diphenyl(Trimethylsilyl)Phosphine. Inorganic Syntheses. 1977, 17: 186–188. doi:10.1002/9780470132487.ch51.

[Bianco-4] 4.0 ^4.1 V. D. Bianco, S. Doronzo. Diphenylphosphine. Inorganic Syntheses. 1976, 16: 161–188. doi:10.1002/9780470132470.ch43.

[5] W. Levason, C. A. Mcauliffe. Cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine. Inorganic Syntheses. 1976, 16: 188–192. doi:10.1002/9780470132470.ch50.

[6] Cao, Guangxiu; Ma, Huailing; Li, Guanliang; Li, Jiqin. Study on synthesis of 1,6-bis(diphenylphosphinel)hexane. Huaxue Yanjiu Yu Yingyong, 2006. 18 (12): 1464-1468.

[7] Plenat, Francoise; Cahyono, Bambang; Cristau, Henri-Jean. Lithium diphenylphosphide: a new demethylation reagent for methylammonium salts. Comptes Rendus de l'Academie des Sciences, Serie IIb: Mecanique,Physique, Chimie, Astronomie, 1995. 320 (10): 539-543. ISSN: 1251-8069.

[8] Alcalde, Maria Isabel; de la Mata, Javier; Gómez, Manuel; Royo, pascual; Sánchez, Fernando. Half-sandwich isocyanide, phosphine, methyl and phosphanido pentamethylcyclopentadienylniobium (V) complexes. Journal of Organometallic Chemistry. 1995, 492 (2): 151–155. ISSN 0022-328X. doi:10.1016/0022-328X(94)05289-N.

[9] Cano, Ana; Cuenca, Tomás; Galakhov, Mikhail; Rodríguez, Gema M.; Royo, Pascual; Cardin, Christine J.; Convery, Maire A. Fulvalene titanium and zirconium complexes: synthesis and NMR study of phosphanido-, alkyl-, and alkynyl-derivatives. X-ray crystal structures of [{Ti(η5−C₅H₅)(μ−PPH₂)}₂{μ−(η5−C₅H₄−η5−C₅H₄)}] and [{Zr(η5−C₅H₅)(μ−C≡CSiMe₃)}₂{μ−(η5−C₅H₄−η5−C₅H₄)}]. Journal of Organometallic Chemistry. 1995, 493 (1-2): 17–25. ISSN 0022-328X. doi:10.1016/0022-328X(94)05288-M.

[10] Issleib, Kurt; Froehlich, Hans Otto. Alkali metal-phosphorus compounds and their reactive behavior. XIII. Preparation and properties of zinc and cuprous diphenylphosphide. Chemische Berichte, 1962. 95: 375-380. ISSN: 0009-2940.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]