Lead(IV) acetate

Lead(IV) acetate

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Names
IUPAC name Lead(IV) acetate
Other names Lead tetraacetate
Identifiers
CAS Number	546-67-8 Y
ChEBI	CHEBI:77245 N
Jmol 3D model	Interactive image
PubChem	11025
InChI InChI=1S/4C2H4O2.Pb/c4*1-2(3)4;/h4*1H3,(H,3,4);/q;;;;+4/p-4 N Key: JEHCHYAKAXDFKV-UHFFFAOYSA-J N
SMILES CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O
Properties
Chemical 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 (347 °F; 448 K)
Boiling point	decomposes
Solubility in water	reacts with water
Solubility	reacts with ethanol soluble in chloroform, benzene, nitrobenzene, hot acetic acid, HCl, tetrachloroethane
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.

Structure

In the solid state the lead atoms are surrounded 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.

Preparation

It can be prepared by reaction of red lead with acetic acid. 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 and the conversion of α-pinene to verbenone
• an alternative reagent to bromine in Hofmann rearrangement
• oxidation of hydrazones to diazo compounds for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane
• aziridine formation, for example the reaction of N-aminophthalimide and stilbene
• cleavage of α-hydroxy acids or 1,2-diols to their corresponding aldehydes or ketones, often replacing ozonolysis; for instance, the oxidation of di-n-butyl d-tartrate to n-butyl glyoxylate.
• reaction with alkenes to form γ-lactones
• oxidation of alcohols carrying a δ-proton to cyclic ethers.
• Oxidative cleavage of certain allyl alcohols in conjunction with ozone:

oxidative cleavage of allyl alcohols

• conversion of acetophenones to phenyl acetic acids
• Decarboxylation of carboxylic acids to alkyl halides in the Kochi reaction

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.

References

Salts and the ester of the Acetate ion
AcOH																	He
LiOAc	Be(OAc)2 BeAcOH											B(OAc)3	ROAc	NH4OAc	AcOAc	FAc	Ne
NaOAc	Mg(OAc)2											Al(OAc)3 ALSOL Al(OAc)2OH	Si	P	S	ClAc	Ar
KOAc	Ca(OAc)2	Sc(OAc)3	Ti(OAc)4	VO(OAc)3	Cr(OAc)2	Mn(OAc)2 MnAc3	Fe(OAc)2 FeAc3	Co(OAc)2, CoAc3	Ni(OAc)2	Cu(OAc)2	Zn(OAc)2	Ga(OAc)3	Ge	As	Se	BrAc	Kr
RbOAc	Sr(OAc)2	Y(OAc)3	Zr(OAc)4	Nb	Mo(OAc)2	Tc	Ru(OAc)2 Ru(OAc)3 Ru(OAc)4	Rh2(OAc)4	Pd(OAc)2	AgOAc	Cd(OAc)2	In	Sn(OAc)2 SnAc4	Sb(OAc)3	Te	IAc	Xe
CsOAc	Ba(OAc)2		Hf	Ta	W	Re	Os	Ir	Pt(OAc)2	Au	Hg2(OAc)2, HgAc2	TlOAc Tl(OAc)3	Pb(OAc)2 Pb(OAc)4	Bi(OAc)3	Po	At	Rn
Fr	Ra		Rf	Db	Sg	Bh	Hs	Mt	Ds	Rg	Cn	Uut	Fl	Uup	Lv	Uus	Uuo
		↓
		La(OAc)3	Ce(OAc)x	Pr	Nd	Pm	Sm(OAc)3	Eu(OAc)3	Gd(OAc)3	Tb	Dy(OAc)3	Ho(OAc)3	Er	Tm	Yb(OAc)3	Lu(OAc)3
		Ac	Th	Pa	UO2(OAc)2	Np	Pu	Am	Cm	Bk	Cf	Es	Fm	Md	No	Lr