Lead(IV) acetate
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| Names | |
|---|---|
| IUPAC name
Lead(IV) acetate
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| Systematic IUPAC name
Tetrakis(acetyloxy)plumbane | |
| Other names
Lead tetraacetate
Plumbic acetate | |
| Identifiers | |
3D model (
JSmol ) |
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| ChEBI | |
| ChemSpider | |
ECHA InfoCard
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100.008.099 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
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Toxic |
| GHS labelling:[1] | |
  
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| Danger | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lead(IV) acetate or lead tetraacetate is an
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]
- 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
organolead compounds. Some of its many uses in organic chemistry
:
- Acetoxylation of benzylic, allylic and α-oxygen ether C−H bonds, for example the
- An alternative reagent to bromine in Hofmann rearrangement[8]
- Oxidation of diazo compounds, for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane[9]
- Aziridine formation, for example the reaction of N-aminophthalimide and stilbene[10]
- glyoxylate.[12]
- Reaction with alkenes to form γ-lactones
- Oxidation of alcohols carrying a δ-proton to cyclic ethers.[13]
- Oxidative cleavage of certain allyl alcohols in conjunction with ozone:[14][15]
- Transformation of 1,2-dicarboxylic acids or cyclic anhydrides to alkenes
- Conversion of acetophenones to phenyl acetic acids[16]
- alkyl halides in the Kochi reaction[17]
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
- ^ "Substance Information - ECHA". echa.europa.eu.
- ISBN 978-0-471-93623-7.
- ISSN 0108-2701.
- ISBN 978-0-470-13232-6.
- S2CID 96821219. Retrieved 19 December 2013.
- ^ Organic Syntheses, Vol. 82, p.99 (2005) Article.
- ^ Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995) Article
- .
- ^ Organic Syntheses, Coll. Vol. 6, p.161 (1988); Vol. 50, p.6 (1970) Article.
- ^ Organic Syntheses, Coll. Vol. 6, p.56 (1988); Vol. 55, p.114 (1976) Link
- doi:10.1246/bcsj.9.8.
- ^ Organic Syntheses, Coll. Vol. 4, p.124 (1963); Vol. 35, p.18 (1955) Article.
- ISBN 0-471-58589-0)
- .
- ^ 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.
- .
- .