Lead(IV) acetate

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IUPACName = Lead(IV) acetate
OtherNames = Lead tetraacetate
Section1 = Chembox Identifiers
CASNo = 546-67-8
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Section2 = Chembox Properties
Formula = Pb(C₂H₃O₂)₄
MolarMass = 443.38 g/mol
Appearance =
Density = 2.23 g/cm³
MeltingPt = 175 - 180C °C
BoilingPt = decomp
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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.

It can be prepared by reaction of red lead with acetic acid [Source: designer-drugs.com [http://www.designer-drugs.com/pte/12.162.180.114/dcd/chemistry/lead.tetraacetate.html Link] .] The other main lead acetate is Lead(II) acetate.

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 [Organic Syntheses, Vol. 82, p.99 (2005) [http://www.orgsynth.org/orgsyn/prep.asp?prep=v82p0099 Article] .] and the conversion of α-pinene to verbenone [Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv9p0745 Article] ]
* oxidation of hydrazones to diazo compounds for example that of "hexafluoroacetone hydrazone" to "bis(trifluoromethyl)diazomethane" [Organic Syntheses, Coll. Vol. 6, p.161 (1988); Vol. 50, p.6 (1970) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv6p0161 Article] .]
* aziridine formation, for example the reaction of N-aminophthalimide and stilbene [Organic Syntheses, Coll. Vol. 6, p.56 (1988); Vol. 55, p.114 (1976) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv6p0056 Link] ]
* 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 [Organic Syntheses, Coll. Vol. 4, p.124 (1963); Vol. 35, p.18 (1955) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv4p0124 Article] .]
* reaction with alkenes to γ-lactones
* oxidation of alcohols carrying a δ-proton to cyclic ethers [ M B Smith, J March. "March's Advanced Organic Chemistry" (Wiley, 2001) (ISBN 0-471-58589-0)] .
* Oxidative cleavage of certain allyl alcohols in conjunction with ozone [ "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] :

* conversion of acetophenones to phenyl acetic acids ["Synthesis" 1981, "2", 126-127.]

References