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Lead(IV) acetate

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 ^[1] 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 ^[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] :

^ Source: designer-drugs.com Link.
^ 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.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Lead(IV)_acetate". A list of authors is available in Wikipedia.