Lithium diphenylphosphide

Lithium diphenylphosphide contains lithium and the organophosphorus anion with the formula (C6H5)2PLi. It is an air-sensitive solid that is used in the preparation of diphenylphosphino compounds. As an ether complex, the lithium salt is dark red.

Part of the polymeric structure of LiPPh2(Et2O).[1]
Lithium diphenylphosphide
Names
Preferred IUPAC name
Lithium diphenylphosphanide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H10P.Li/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;/h1-10H;/q-1;+1
    Key: WKUYEGHEUWHKIU-UHFFFAOYSA-N
  • [Li+].C1=CC=C(C=C1)[P-]C2=CC=CC=C2
Properties
C12H10LiP
Molar mass 192.13 g·mol−1
Appearance pale yellow solid
Reacts with water
Solubility Ethers, hydrocarbons
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H302, H312, H314, H332, H410
P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis and reactions

The lithium, sodium, and potassium salts are prepared by reduction of chlorodiphenylphosphine,[2] triphenylphosphine,[3][4] or tetraphenyldiphosphine with alkali metals (M):

(C6H5)2PCl + 2 M → (C6H5)2PM + MCl
(C6H5)3P + 2 M → (C6H5)2PM + MC6H5
(C6H5)4P2 + 2 M → 2 (C6H5)2PM

They can also be obtained by deprotonation of diphenylphosphine.

With water, the salts convert to diphenylphosphine:[4]

(C6H5)2PLi + H2O → (C6H5)2PH + LiOH

With halocarbons, the salts react to give tertiary phosphines:[5]

(C6H5)2PM + RX → (C6H5)2PR + MX

When treated with metal halides, lithium diphenylphosphide gives transition metal phosphido complexes.

Structure

Although treated as salts, alkali diphenylphosphides are highly aggregated in solution. They adopt polymeric structures as solids.

  • Sodium diphenylphosphide (CAS RN 4376-01-6)
  • Potassium diphenylphosphide (CAS RN 15475-27-1)

References
  1. Ruth A. Bartlett, Marilyn M. Olmstead, Philip P. Power (1986). "Structural Characterization of the Solvate Complexes of the Lithium Diorganophosphides [{Li(Et2O)PPh2}∞], [{Li(THF)2PPh2}∞], and [{Li(THF)P(C6H11)2}∞]". Inorg. Chem. 25: 1243–1247. doi:10.1021/ic00228a034.{{cite journal}}: CS1 maint: uses authors parameter (link)
  2. R. Goldsberry Kim Cohn (1972). "Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)-phosphine". Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)‐phosphine. Inorganic Syntheses. Vol. 13. pp. 26–32. doi:10.1002/9780470132449.ch7. ISBN 9780470132449.{{cite book}}: CS1 maint: uses authors parameter (link)
  3. George W. Luther, III, Gordon Beyerle (1977). "Lithium Diphenylphosphide and Diphenyl(Trimethylsilyl)Phosphine". Inorganic Syntheses. Inorganic Syntheses. Vol. 17. pp. 186–188. doi:10.1002/9780470132487.ch51. ISBN 9780470132487.{{cite book}}: CS1 maint: uses authors parameter (link)
  4. V. D. Bianco, S. Doronzo (1976). "Diphenylphosphine". Inorganic Syntheses. Inorganic Syntheses. Vol. 16. pp. 161–188. doi:10.1002/9780470132470.ch43. ISBN 9780470132470.{{cite book}}: CS1 maint: uses authors parameter (link)
  5. W. Levason, C. A. Mcauliffe (1976). "Cis -2-Diphenylarsinovinyldiphenylphosphine and 2-Diphenylarsinoethyldiphenylphosphine". Cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine. Inorganic Syntheses. Vol. 16. pp. 188–192. doi:10.1002/9780470132470.ch50. ISBN 9780470132470.{{cite book}}: CS1 maint: uses authors parameter (link)
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