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Lead(IV) acetate is an important oxidizing agent and a source of acetyloxy group used in organic synthesis. For example, 1,4-dioxene is prepared from dioxane involving 2-acetoxy-1,4-dioxane as an intermediate. Similarly, it is used for the preparation of bis(trifluoromethyl)diazomethane from hexafluoroacetone hydrazone. It also reacts with alkenes, alcohols having a delta-proton and di-n-butyl d-tartrate to get gamma-lactones, cyclic ethers and n-butyl glyoxylate respectively. It induces the cleavage of 1,2-diols to the corresponding aldehydes or ketones. It is actively involved in the Kochi reaction for the decarboxylation of carboxylic acids to alkyl halides and used as an alternative reagent to bromine in the Hofmann rearrangement.
Versatile oxidizing agent and source of acetoxy radicals. For a review of one-step acetoxylation at carbon, see: Synthesis, 567 (1973). See also: M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph 186, Washington DC (1990). Oxidizes silyl enol ethers to ɑ-acetoxycarbonyl compounds in high yields: Tetrahedron, 39, 861 (1983). In combination with a metal halide, enol ethers are similarly converted to ɑ-halocarbonyl compounds: Synthesis, 1021 (1982).
Cleaves vic-glycols to carbonyl compounds; see, e.g.: Org. Synth. Coll., 4, 124 (1963).
N-Formylanilines are oxidized to isocyanates. In the presence of methanol, the reaction affords the methyl urethanes directly: Synthesis, 225 (1982).
Carboxylic acids undergo oxidative decarboxylation; review: Org. React., 19, 279 (1972). In the presence of LiCl, the alkyl chloride is obtained (Kochi reaction): J. Am. Chem. Soc., 87, 2500 (1965); Synth. Commun., 20, 1011 (1990). Yields are lower for the bromide and iodide, cf Hunsdiecker reaction (see Mercury(II) oxide, A16157). Use of NCS allows successful scale-up: Synthesis, 493 (1973).
Intramolecular oxidative cyclization of alcohols with the reagent leads to tetrahydrofurans or tetrahydropyrans, a useful method for the functionalization of remote positions; review: Synthesis, 279 (1970). For a review of the hypoiodite method for the functionalization of remote positions such as the angular methyl groups of steroids, e.g. by reaction with lead tetraacetate and iodine, see: Synthesis, 501 (1971). For use in the synthesis of protoadamantane, see: Org. Synth. Coll., 6, 958 (1988). Compare Iodosobenzene diacetate, B24531.
For use in dichloroacetic acid for the plumbation of activated aromatics to form aryllead(IV) triacetates, which are useful arylating agents for active methylene groups under very mild conditions, see: Org. Synth. Coll., 7, 229 (1990). For N-arylation of amides, see: J. Org. Chem., 61, 5865 (1996). Arylboronic acids also give aryllead(IV) triacetates, used in situ for electrophilic arylation: J. Chem. Soc., Perkin 1, 715 (1990). For a review of the use of organolead(IV) triacetates in synthesis, see: Pure Appl. Chem., 68, 819 (1996).
-Hydroxystannanes undergo oxidative fragmentation in a synthesis of unsaturated macrolides: Org. Synth. Coll., 8, 562 (1993).
You, X.; Li, F. B.; Wang, G. W. Synthesis of Ortho Acid Ester-Type 1, 3-Dioxolanofullerenes: Radical Reaction of  Fullerene with Halocarboxylic Acids Promoted by Lead (IV) Acetate. J. Org. Chem. 2014, 79 (22), 11155-11160.
Sun, X.; Yang, J.; Zhang, W.; Zhu, X.; Hu, Y.; Yang, D.; Yuan, X.; Yu, W.; Dong, J.; Wang, H.; Li, L.; Vasant Kumar, R.; Liang, S. Lead acetate trihydrate precursor route to synthesize novel ultrafine lead oxide from spent lead acid battery pastes. J. Power Sources 2014, 269, 565-576.
Gefahrenhinweise (EU): H302-H332-H360-H373
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