Lead(IV) acetate
| Lead(IV) acetate | |
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Lead(IV) acetate |
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Other names
Lead tetraacetate |
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| Identifiers | |
| CAS number | 546-67-8  |
| PubChem | 11025 |
| Properties | |
| Molecular formula | 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 |
| Boiling point |
decomp |
| Solubility in water | reacts |
| Solubility | reacts with ethanol soluble in chloroform, benzene, nitrobenzene, hot acetic acid, HCl, tetrachloroethane |
| Hazards | |
| NFPA 704 |
 0
3
0
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Lead(IV) acetate or lead tetraacetate is a chemical compound with chemical formula Pb(C2H3O2)4 and is a lead salt of acetic acid. It is commercially available often stabilized with acetic acid.
Contents |
[edit] Preparation
It can be prepared by reaction of red lead with acetic acid [1] The other main lead acetate is lead(II) acetate.
[edit] Reagent in organic chemistry
Lead tetraacetate is a strong oxidizing agent, 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:
- acetoxylation of benzylic, allylic and α-oxygen ether C-H bonds, for example the photochemical conversion of dioxane to 1,4-dioxene through the 2-acetoxy-1,4-dioxane intermediate [2] and the conversion of α-pinene to verbenone [3]
- oxidation of hydrazones to diazo compounds for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane [4]
- aziridine formation, for example the reaction of N-aminophthalimide and stilbene [5]
- cleavage of 1,2-diols to the corresponding aldehydes or ketones often replacing ozonolysis, for instance the oxidation of di-n-butyl d-tartrate to n-butyl glyoxylate [6]
- reaction with alkenes to γ-lactones
- oxidation of alcohols carrying a δ-proton to cyclic ethers [7].
- Oxidative cleavage of certain allyl alcohols in conjunction with ozone [8] [9] :
- conversion of acetophenones to phenyl acetic acids [10]
[edit] 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.
[edit] References
- ^ Inorg. Synth, 1, 47 (1939).
- ^ 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
- ^ 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) (ISBN 0-471-58589-0)
- ^ 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
- ^ 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
- ^ Synthesis 1981, 2, 126-127.
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