Lead(IV) acetate
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| Molar mass | 443.376 g/mol |
| Appearance | colorless or pink columnar crystals |
| Odor | vinegar |
| Density | 2.228 g/cm3 (17 °C) |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Solubility | Reacts with ethanol. Soluble in chloroform, benzene, nitrobenzene, hot acetic acid, HCl(aq), tetrachloroethane. |
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Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Template:Chem2, often abbreviated as Template:Chem2, where Ac is acyl. 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.[1]
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 (Template:Chem2), which absorbs water. The net reaction is shown:[3][4]
The remaining lead(II) acetate can be partially oxidized to the tetraacetate by Cl2, with a [[Lead(II) chloride|Template:Chem2]] by-product:
Reagent in organic chemistry
Lead tetraacetate is a strong oxidizing agent,[5] a source of acetyloxy groups, and a general reagent for the preparation of organolead compounds. Some of its many uses in organic chemistry:
- Acetoxylation of benzylic, allylic,[6] and α-oxygen ether C−H bonds, for example the conversion of dioxane to 2-acetoxy-1,4-dioxane [7]
- An alternative reagent to bromine in Hofmann rearrangement[8]
- Dehydrogenation of hydrazones and hydrazines, for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane[9][10]
- Cleavage of α-hydroxy acids[11] or 1,2-diols to their corresponding aldehydes or ketones, often replacing ozonolysis; for instance, the oxidation of di-n-butyl Template:Sc-tartrate to n-butyl 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]
- Decarboxylation of carboxylic acids to alkyl halides in the Kochi reaction[17]
Safety
Lead(IV) acetate is toxic, because of lead. It is a neurotoxin. It badly affects the gum tissue, central nervous system, kidneys, blood, and reproductive system.
References
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- ↑ Organic Syntheses, Vol. 82, p. 99 (2005) Article.
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- ↑ Organic Syntheses, Coll. Vol. 4, p. 124 (1963); Vol. 35, p. 18 (1955) Article.
- ↑ M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) (Template:ISBN)
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- ↑ 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.
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