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Lead(IV) acetate

Lead(IV) acetate
Names
IUPAC name
Lead(IV) acetate
Systematic IUPAC name
Tetrakis(acetyloxy)plumbane
Other names
Lead tetraacetate
Plumbic acetate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.099 Edit this at Wikidata
EC Number
  • 208-908-0
UNII
  • InChI=1S/4C2H4O2.Pb/c4*1-2(3)4;/h4*1H3,(H,3,4);/q;;;;+4/p-4 ☒N
    Key: JEHCHYAKAXDFKV-UHFFFAOYSA-J ☒N
  • monodentate acetate: CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O
  • bidentate acetate: O0[C-](C)O[Pb+4]0123(O[C-](C)O1)(O[C-]C(C)O2)O[C-](C)O3
Properties
Pb(C2H3O2)4
Molar mass 443.376 g/mol
Appearance colorless or pink crystals
Odor vinegar
Density 2.228 g/cm3 (17 °C)
Melting point 175 °C (347 °F; 448 K)
Boiling point decomposes
soluble, reversible hydrolysis
Solubility reacts with ethanol
soluble in chloroform, benzene, nitrobenzene, hot acetic acid, HCl, tetrachloroethane
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
GHS labelling:[1]
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Pb(C2H3O2)4. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis.[2]

Structure

In the solid state the lead(IV) centers are coordinated by four acetate ions, which are bidentate, each coordinating via two oxygen atoms. The lead atom is 8 coordinate and the O atoms form a flattened trigonal dodecahedron.[3]

Preparation

It is typically prepared by treating of red lead with acetic acid and acetic anhydride (Ac2O), which absorbs water. The net reaction is shown:[4][5]

Pb3O4 + 4 Ac2O → Pb(OAc)4 + 2 Pb(OAc)2

The remaining lead(II) acetate can be partially oxidized to the tetraacetate by Cl2, with a PbCl2 by-product:

2 Pb(OAc)2 + Cl2 → Pb(OAc)4 + PbCl2

Reagent in organic chemistry

Lead tetraacetate is a strong oxidizing agent,[6] a source of acetyloxy groups, and a general reagent for the preparation of organolead compounds. Some of its many uses in organic chemistry:

oxidative cleavage of allyl alcohols
oxidative cleavage of allyl alcohols

Safety

Lead(IV) acetate is toxic. It is a neurotoxin. It affects the gum tissue, central nervous system, kidneys, blood, and reproductive system.

References

  1. ^ "Substance Information - ECHA". echa.europa.eu.
  2. ^ Mihailo Lj. Mihailović; Živorad Čeković; Brian M. Mathes (2005). "Lead(IV) Acetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rl006.pub2. ISBN 978-0-471-93623-7.
  3. ^ Schürmann, M.; Huber, F. (1994). "A redetermination of lead(IV) acetate". Acta Crystallographica Section C. 50 (11): 1710–1713. doi:10.1107/S0108270194006438. ISSN 0108-2701.
  4. ^ J. C. Bailar, Jr. (1939). "Lead Tetracetate". Inorganic Syntheses. Inorganic Syntheses. Vol. 1. pp. 47–49. doi:10.1002/9780470132326.ch17. ISBN 978-0-470-13232-6.
  5. ^ M. Baudler (1963). "Lead(IV) Acetate". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 2. NY,NY: Academic Press. p. 767.
  6. ^ J. Zýka (1966). "Analytical study of the basic properties of lead tetraacetate as oxidizing agent" (PDF). Pure and Applied Chemistry. 13 (4): 569–581. doi:10.1351/pac196613040569. S2CID 96821219. Retrieved 19 December 2013.
  7. ^ "(1R,5R)-(+)-Verbenone of High Optical Purity". Organic Syntheses. 72: 57. 1995. doi:10.15227/orgsyn.072.0057.
  8. ^ Organic Syntheses, Vol. 82, p.99 (2005) Article.
  9. ^ Baumgarten, Henry; Smith, Howard; Staklis, Andris (1975). "Reactions of amines. XVIII. Oxidative rearrangement of amides with lead tetraacetate". The Journal of Organic Chemistry. 40 (24): 3554–3561. doi:10.1021/jo00912a019.
  10. ^ Middleton, W. J.; Gale, D. M. (1970). "Bis(Trifluoromethyl)Diazomethane". Organic Syntheses. 50: 6. doi:10.15227/orgsyn.050.0006.
  11. ^ Robert K. Muller, Renato Joos, Dorothee Felix, Jakob Schreiber, Claude Wintner, and A. Eschenmoser (1976). "Preparation of N-Aminoaziridines: trans-1-Amino-2,3-diphenylaziridine, 1-Amino-2-phenylaziridine, and 1-Amino-2-phenylaziridinium Acetate". Organic Syntheses. 55: 114. doi:10.15227/orgsyn.055.0114.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  12. ^ Ōeda, Haruomi (1934). "Oxidation of some α-hydroxy-acids with lead tetraacetate". Bulletin of the Chemical Society of Japan. 9 (1): 8–14. doi:10.1246/bcsj.9.8.
  13. ^ Organic Syntheses, Coll. Vol. 4, p.124 (1963); Vol. 35, p.18 (1955) Article.
  14. ^ M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN 0-471-58589-0)
  15. ^ Álvarez Manzaneda, E. J.; Chahboun, R.; Cano, M. J.; Cabrera Torres, E.; Álvarez, E.; Álvarez Manzaneda, R.; Haidour, A.; Ramos López, J. M. (2006). "O3/Pb(OAc)4: a new and efficient system for the oxidative cleavage of allyl alcohols". Tetrahedron Letters. 47 (37): 6619–6622. doi:10.1016/j.tetlet.2006.07.020.
  16. ^ Conversion of 1-allylcyclohexanol to cyclohexanone, in the proposed reaction mechanism the allyl group is first converted to a trioxalane according to conventional ozonolysis which then interacts with the alkoxy lead group.
  17. ^ Myrboh, B.; Ila, H.; Junjappa, H. (1981). "One-Step Synthesis of Methyl Arylacetates from Acetophenones Using Lead(IV) Acetate". Synthesis. 2 (2): 126–127. doi:10.1055/s-1981-29358.
  18. ^ Jay K. Kochi (1965). "A New Method for Halodecarboxylation of Acids Using Lead(IV) Acetate". J. Am. Chem. Soc. 87 (11): 2500–02. doi:10.1021/ja01089a041.
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