Lead(IV) acetate

Lead(IV) acetate or lead tetraacetate is a chemical compound with chemical formula Pb(C2H3O2)4. It is a colorless solid that is soluble in nonpolar organic solvents, indicative 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.[1]

Lead(IV) acetate
Names
IUPAC name
Lead(IV) acetate
Other names
Lead tetraacetate
Plumbic acetate
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard 100.008.099
UNII
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
Main hazards Toxic
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
3
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 YN ?)
Infobox references

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.[2]

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:[3]

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

The remaining lead(II) acetate can be partially oxidized to the tetraacetate:

2 Pb(OAc)2 + Cl2 → Pb(OAc)4 + PbCl2

Reagent in organic chemistry

Lead tetraacetate is a strong oxidizing agent,[4] a source of acetyloxy groups and a general reagent for the introduction of lead into organolead compounds. Some of its many uses in organic chemistry:

oxidative cleavage of allyl alcohols

Safety

Lead(IV) acetate may be fatal if ingested, inhaled, or absorbed through skin. It causes irritation to skin, eyes, and respiratory tract. It is a neurotoxin. It affects the gum tissue, central nervous system, kidneys, blood, and reproductive system.

References
  1. Mihailo Lj. Mihailović, Živorad Čeković, Brian M. Mathes (2005). "Lead(IV) Acetate". Encyclopedia of Reagents for Organic Synthesis, 8 Volume Set. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rl006.pub2. ISBN 978-0471936237.CS1 maint: uses authors parameter (link)
  2. 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.
  3. J. C. Bailar, Jr. (1939). Lead Tetracetate. Inorganic Syntheses. 1. pp. 47–49. doi:10.1002/9780470132326.ch17. ISBN 9780470132326.
  4. 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. Retrieved 19 December 2013.
  5. Organic Syntheses, Vol. 82, p.99 (2005) Article.
  6. Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995) Article
  7. 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.
  8. Organic Syntheses, Coll. Vol. 6, p.161 (1988); Vol. 50, p.6 (1970) Article.
  9. Organic Syntheses, Coll. Vol. 6, p.56 (1988); Vol. 55, p.114 (1976) Link
  10. Ôeda, 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.
  11. Organic Syntheses, Coll. Vol. 4, p.124 (1963); Vol. 35, p.18 (1955) Article.
  12. M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN 0-471-58589-0)
  13. O3/Pb(OAc)4: a new and efficient system for the oxidative cleavage of allyl alcohols E.J. Alvarez-Manzaneda R. Chahboun , M.J. Cano, E. Cabrera Torres, E. Alvarez, R. Alvarez-Manzaneda, b, A. Haidour and J.M. Ramos López Tetrahedron Letters Volume 47, Issue 37 , 11 September 2006, Pages 6619-6622 doi:10.1016/j.tetlet.2006.07.020
  14. Conversion of 1-allyl-cyclohexanol 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
  15. 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.
  16. 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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