Lead(IV) acetate: Difference between revisions

Lead(IV) acetate
Names
	IUPAC name Lead(IV) acetate
	Systematic IUPAC name Tetrakis(acetyloxy)plumbane
	Other names Lead tetraacetate; Plumbic acetate
Identifiers
CAS Number	546-67-8 ;
3D model (JSmol)	monodentate acetate: Interactive image; bidentate acetate: Interactive image;
ChEBI	CHEBI:77245 ;
ChemSpider	10608816;
ECHA InfoCard	100.008.099
EC Number	208-908-0;
PubChem CID	11025;
UNII	CFN24B03DB ;
CompTox Dashboard (EPA)	DTXSID801047756 DTXSID6041058, DTXSID801047756 ;
	InChI InChI=1S/4C2H4O2.Pb/c41-2(3)4;/h41H3,(H,3,4);/q;;;;+4/p-4 Key: JEHCHYAKAXDFKV-UHFFFAOYSA-J ;
	SMILES monodentate acetate: CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O; bidentate acetate: O0[C-](C)O[Pb+4]0123(O[C-](C)O1)(O[C-]C(C)O2)O[C-](C)O3;
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	soluble, reversible hydrolysis
Solubility	reacts with ethanol ; soluble in chloroform, benzene, nitrobenzene, hot acetic acid, HCl, tetrachloroethane
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic
	GHS labelling:
Pictograms
Signal word	Danger
NFPA 704 (fire diamond)	3 0 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Lead(IV) acetate or lead tetraacetate is an metalorganic compound with chemical formula Pb(C₂H₃O₂)₄. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis.^[2]

Structure

In the solid state the lead(IV) centers are coordinated 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.^[3]

Preparation

It is typically prepared by treating of red lead with acetic acid and acetic anhydride (Ac₂O), which absorbs water. The net reaction is shown:^[4]^[5]

Pb₃O₄ + 4 Ac₂O → Pb(OAc)₄ + 2 Pb(OAc)₂

The remaining lead(II) acetate can be partially oxidized to the tetraacetate by Cl₂, with a PbCl₂ by-product:

2 Pb(OAc)₂ + Cl₂ → Pb(OAc)₄ + PbCl₂

Reagent in organic chemistry

Lead tetraacetate is a strong oxidizing agent,^[6] a source of acetyloxy groups, and a general reagent for the preparation of organolead compounds. Some of its many uses in organic chemistry:

Acetoxylation of benzylic, allylic,^[7] and α-oxygen ether C−H bonds, for example the conversion of dioxane to 2-acetoxy-1,4-dioxane ^[8]
An alternative reagent to bromine in Hofmann rearrangement^[9]
Dehydrogenation of hydrazones and hydrazines, for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane^[10]^[11]
Cleavage of α-hydroxy acids^[12] 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.^[13]
Reaction with alkenes to form γ-lactones
Oxidation of alcohols carrying a δ-proton to cyclic ethers.^[14]
Oxidative cleavage of certain allyl alcohols in conjunction with ozone:^[15]^[16]
Transformation of 1,2-dicarboxylic acids or cyclic anhydrides to alkenes

Conversion of acetophenones to phenyl acetic acids^[17]
Decarboxylation of carboxylic acids to alkyl halides in the Kochi reaction^[18]

Safety

Lead(IV) acetate is toxic. It is a neurotoxin. It affects the gum tissue, central nervous system, kidneys, blood, and reproductive system.

References

^ "Substance Information - ECHA". echa.europa.eu.
^ Mihailo Lj. Mihailović; Živorad Čeković; Brian M. Mathes (2005). "Lead(IV) Acetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rl006.pub2. ISBN 978-0-471-93623-7.
^ Schürmann, M.; Huber, F. (1994). "A redetermination of lead(IV) acetate". Acta Crystallographica Section C. 50 (11): 1710–1713. doi:10.1107/S0108270194006438. ISSN 0108-2701.
^ J. C. Bailar, Jr. (1939). "Lead Tetracetate". Inorganic Syntheses. Inorganic Syntheses. Vol. 1. pp. 47–49. doi:10.1002/9780470132326.ch17. ISBN 978-0-470-13232-6.
^ M. Baudler (1963). "Lead(IV) Acetate". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 2. NY,NY: Academic Press. p. 767.
^ J. Zýka (1966). "Analytical study of the basic properties of lead tetraacetate as oxidizing agent" (PDF). Pure and Applied Chemistry. 13 (4): 569–581. doi:10.1351/pac196613040569. S2CID 96821219. Retrieved 19 December 2013.
^ "(1R,5R)-(+)-Verbenone of High Optical Purity". Organic Syntheses. 72: 57. 1995. doi:10.15227/orgsyn.072.0057.
^ Organic Syntheses, Vol. 82, p.99 (2005) Article.
^ Baumgarten, Henry; Smith, Howard; Staklis, Andris (1975). "Reactions of amines. XVIII. Oxidative rearrangement of amides with lead tetraacetate". The Journal of Organic Chemistry. 40 (24): 3554–3561. doi:10.1021/jo00912a019.
^ Middleton, W. J.; Gale, D. M. (1970). "Bis(Trifluoromethyl)Diazomethane". Organic Syntheses. 50: 6. doi:10.15227/orgsyn.050.0006.
^ Robert K. Muller, Renato Joos, Dorothee Felix, Jakob Schreiber, Claude Wintner, and A. Eschenmoser (1976). "Preparation of N-Aminoaziridines: trans-1-Amino-2,3-diphenylaziridine, 1-Amino-2-phenylaziridine, and 1-Amino-2-phenylaziridinium Acetate". Organic Syntheses. 55: 114. doi:10.15227/orgsyn.055.0114.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Ōeda, Haruomi (1934). "Oxidation of some α-hydroxy-acids with lead tetraacetate". Bulletin of the Chemical Society of Japan. 9 (1): 8–14. doi:10.1246/bcsj.9.8.
^ 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)
^ Álvarez Manzaneda, E. J.; Chahboun, R.; Cano, M. J.; Cabrera Torres, E.; Álvarez, E.; Álvarez Manzaneda, R.; Haidour, A.; Ramos López, J. M. (2006). "O₃/Pb(OAc)₄: a new and efficient system for the oxidative cleavage of allyl alcohols". Tetrahedron Letters. 47 (37): 6619–6622. doi:10.1016/j.tetlet.2006.07.020.
^ Conversion of 1-allylcyclohexanol 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.
^ Myrboh, B.; Ila, H.; Junjappa, H. (1981). "One-Step Synthesis of Methyl Arylacetates from Acetophenones Using Lead(IV) Acetate". Synthesis. 2 (2): 126–127. doi:10.1055/s-1981-29358.
^ Jay K. Kochi (1965). "A New Method for Halodecarboxylation of Acids Using Lead(IV) Acetate". J. Am. Chem. Soc. 87 (11): 2500–02. doi:10.1021/ja01089a041.

[1] "Substance Information - ECHA". echa.europa.eu.

[2] Mihailo Lj. Mihailović; Živorad Čeković; Brian M. Mathes (2005). "Lead(IV) Acetate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rl006.pub2. ISBN 978-0-471-93623-7.

[3] Schürmann, M.; Huber, F. (1994). "A redetermination of lead(IV) acetate". Acta Crystallographica Section C. 50 (11): 1710–1713. doi:10.1107/S0108270194006438. ISSN 0108-2701.

[4] J. C. Bailar, Jr. (1939). "Lead Tetracetate". Inorganic Syntheses. Inorganic Syntheses. Vol. 1. pp. 47–49. doi:10.1002/9780470132326.ch17. ISBN 978-0-470-13232-6.

[5] M. Baudler (1963). "Lead(IV) Acetate". In G. Brauer (ed.). Handbook of Preparative Inorganic Chemistry, 2nd Ed. Vol. 2. NY,NY: Academic Press. p. 767.

[6] J. Zýka (1966). "Analytical study of the basic properties of lead tetraacetate as oxidizing agent" (PDF). Pure and Applied Chemistry. 13 (4): 569–581. doi:10.1351/pac196613040569. S2CID 96821219. Retrieved 19 December 2013.

[7] "(1R,5R)-(+)-Verbenone of High Optical Purity". Organic Syntheses. 72: 57. 1995. doi:10.15227/orgsyn.072.0057.

[8] Organic Syntheses, Vol. 82, p.99 (2005) Article.

[9] Baumgarten, Henry; Smith, Howard; Staklis, Andris (1975). "Reactions of amines. XVIII. Oxidative rearrangement of amides with lead tetraacetate". The Journal of Organic Chemistry. 40 (24): 3554–3561. doi:10.1021/jo00912a019.

[10] Middleton, W. J.; Gale, D. M. (1970). "Bis(Trifluoromethyl)Diazomethane". Organic Syntheses. 50: 6. doi:10.15227/orgsyn.050.0006.

[11] Robert K. Muller, Renato Joos, Dorothee Felix, Jakob Schreiber, Claude Wintner, and A. Eschenmoser (1976). "Preparation of N-Aminoaziridines: trans-1-Amino-2,3-diphenylaziridine, 1-Amino-2-phenylaziridine, and 1-Amino-2-phenylaziridinium Acetate". Organic Syntheses. 55: 114. doi:10.15227/orgsyn.055.0114.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[12] Ōeda, Haruomi (1934). "Oxidation of some α-hydroxy-acids with lead tetraacetate". Bulletin of the Chemical Society of Japan. 9 (1): 8–14. doi:10.1246/bcsj.9.8.

[13] Organic Syntheses, Coll. Vol. 4, p.124 (1963); Vol. 35, p.18 (1955) Article.

[14] M B Smith, J March. March's Advanced Organic Chemistry (Wiley, 2001) (ISBN 0-471-58589-0)

[15] Álvarez Manzaneda, E. J.; Chahboun, R.; Cano, M. J.; Cabrera Torres, E.; Álvarez, E.; Álvarez Manzaneda, R.; Haidour, A.; Ramos López, J. M. (2006). "O₃/Pb(OAc)₄: a new and efficient system for the oxidative cleavage of allyl alcohols". Tetrahedron Letters. 47 (37): 6619–6622. doi:10.1016/j.tetlet.2006.07.020.

[16] Conversion of 1-allylcyclohexanol 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.

[17] Myrboh, B.; Ila, H.; Junjappa, H. (1981). "One-Step Synthesis of Methyl Arylacetates from Acetophenones Using Lead(IV) Acetate". Synthesis. 2 (2): 126–127. doi:10.1055/s-1981-29358.

[18] Jay K. Kochi (1965). "A New Method for Halodecarboxylation of Acids Using Lead(IV) Acetate". J. Am. Chem. Soc. 87 (11): 2500–02. doi:10.1021/ja01089a041.

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@@ Line 1: / Line 1: @@
 {{Short description|Organometallic compound (Pb(C2H3O2)4)}}
 {{chembox
-| Verifiedfields = changed
+|Verifiedfields = changed
-| Watchedfields = changed
+|Watchedfields = changed
-| verifiedrevid = 431950862
+|verifiedrevid = 431950862
-| ImageFile = Lead-tetraacetate-3D-balls.png
+|ImageFile = Lead-tetraacetate-3D-balls.png
-| IUPACName = Lead(IV) acetate
+|IUPACName = Lead(IV) acetate
+|SystematicName = Tetrakis(acetyloxy)plumbane
-| OtherNames = Lead tetraacetate<br/>Plumbic acetate
+|OtherNames = Lead tetraacetate<br/>Plumbic acetate
-| Section1={{Chembox Identifiers
+|Section1={{Chembox Identifiers
-| CASNo_Ref = {{cascite|correct|CAS}}
+|CASNo_Ref = {{cascite|correct|CAS}}
-| CASNo = 546-67-8
+|CASNo = 546-67-8
-| UNII_Ref = {{fdacite|correct|FDA}}
+|ChEBI_Ref = {{ebicite|correct|EBI}}
-| UNII = CFN24B03DB
-| PubChem = 11025
+|ChEBI = 77245
+| ChemSpiderID = 10608816
-| ChEBI_Ref = {{ebicite|changed|EBI}}
-| ChEBI = 77245
+| EINECS = 208-908-0
+|UNII_Ref = {{fdacite|correct|FDA}}
-| SMILES = CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O
+|UNII = CFN24B03DB
-| SMILES_Comment = monodentate acetate
+|PubChem = 11025
-| SMILES1 = o0c(C)[o+][Pb-4]0123([o+]c(C)o1)([o+]c(C)o2)[o+]c(C)o3
+|SMILES = CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O
-| SMILES1_Comment = bidentate acetate
+|SMILES_Comment = monodentate acetate
-| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+|SMILES1 = O0[C-](C)O[Pb+4]0123(O[C-](C)O1)(O[C-]C(C)O2)O[C-](C)O3
-| StdInChI = 1S/4C2H4O2.Pb/c4*1-2(3)4;/h4*1H3,(H,3,4);/q;;;;+4/p-4
+|SMILES1_Comment = bidentate acetate
-| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
-| StdInChIKey = JEHCHYAKAXDFKV-UHFFFAOYSA-J
+|StdInChI = 1S/4C2H4O2.Pb/c4*1-2(3)4;/h4*1H3,(H,3,4);/q;;;;+4/p-4
+|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+|StdInChIKey = JEHCHYAKAXDFKV-UHFFFAOYSA-J
 }}
 |Section2={{Chembox Properties
-| Formula = {{chem2|Pb(C2H3O2)4}}
+|Formula = {{chem2|Pb(C2H3O2)4}}
-| MolarMass = 443.376 g/mol
+|MolarMass = 443.376 g/mol
-| Appearance = colorless or pink crystals
+|Appearance = colorless or pink crystals
-| Odor = vinegar
+|Odor = vinegar
-| Density = 2.228 g/cm<sup>3</sup> (17 °C)
+|Density = 2.228 g/cm<sup>3</sup> (17 °C)
-| MeltingPtC = 175
+|MeltingPtC = 175
-| BoilingPt = decomposes
+|BoilingPt = decomposes
-| Solubility = soluble, reversible hydrolysis
+|Solubility = soluble, reversible hydrolysis
-| SolubleOther = reacts with [[ethanol]] <br> soluble in [[chloroform]], [[benzene]], [[nitrobenzene]], hot [[acetic acid]], [[hydrochloric acid|HCl]], [[tetrachloroethane]]
+|SolubleOther = reacts with [[ethanol]] <br /> soluble in [[chloroform]], [[benzene]], [[nitrobenzene]], hot [[acetic acid]], [[hydrochloric acid|HCl]], [[tetrachloroethane]]
 }}
 |Section3={{Chembox Hazards
+| GHS_ref=<ref>{{cite web |title=Substance Information - ECHA |url=https://echa.europa.eu/substance-information/-/substanceinfo/100.008.099 |website=echa.europa.eu}}</ref>
-| MainHazards = Toxic
+| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
-| NFPA-H = 3
-| NFPA-F = 0
+| GHSSignalWord = Danger
+| HPhrases = {{H-phrases|}}
-| NFPA-R = 0
+| PPhrases = {{P-phrases|}}
- }}
+|MainHazards = Toxic
+|NFPA-H = 3
+|NFPA-F = 0
+|NFPA-R = 0
+}}
 }}
-'''Lead(IV) acetate''' or '''lead tetraacetate''' is an [[organometallic compound]] with [[chemical formula]] {{chem2|Pb(C2H3O2)4}}. It is a colorless solid that is [[soluble]] in [[nonpolar]], [[organic solvent]]s, indicating that it is not a [[Salt (chemistry)|salt]]. It is degraded by moisture and is typically stored with additional [[acetic acid]]. The compound is used in [[organic synthesis]].<ref>{{cite encyclopedia|authors=Mihailo Lj. Mihailović, Živorad Čeković, Brian M. Mathes|encyclopedia=Encyclopedia of Reagents for Organic Synthesis|year=2005|doi=10.1002/047084289X.rl006.pub2|isbn = 978-0471936237|chapter = Lead(IV) Acetate}}</ref>
+'''Lead(IV) acetate''' or '''lead tetraacetate''' is an [[metalorganic compound]] with [[chemical formula]] {{chem2|Pb(C2H3O2)4}}. It is a colorless solid that is [[soluble]] in [[nonpolar]], [[organic solvent]]s, indicating that it is not a [[Salt (chemistry)|salt]]. It is degraded by moisture and is typically stored with additional [[acetic acid]]. The compound is used in [[organic synthesis]].<ref>{{cite encyclopedia|author=Mihailo Lj. Mihailović |author2=Živorad Čeković |author3=Brian M. Mathes |encyclopedia=Encyclopedia of Reagents for Organic Synthesis|year=2005|doi=10.1002/047084289X.rl006.pub2|isbn = 978-0-471-93623-7|chapter = Lead(IV) Acetate}}</ref>
 ==Structure==
-In the solid state the lead(IV) centers are coordinated by four acetate ions, which are [[denticity|bidentate]], each coordinating via two oxygen atoms. The lead atom is 8 coordinate and the O atoms form a flattened [[snub disphenoid|trigonal dodecahedron]].<ref>{{cite journal |last1=Schürmann |first1=M. |last2=Huber |first2=F. |title=A redetermination of lead(IV) acetate |journal=Acta Crystallographica Section C |volume=50 |issue=11 |year=1994 |pages=1710–1713 |issn=0108-2701 |doi=10.1107/S0108270194006438|doi-access=free}}</ref>
+In the solid state the lead(IV) centers are coordinated by four acetate ions, which are [[denticity|bidentate]], each coordinating via two oxygen atoms. The lead atom is 8 coordinate and the O atoms form a flattened [[snub disphenoid|trigonal dodecahedron]].<ref>{{cite journal |last1=Schürmann |first1=M. |last2=Huber |first2=F. |title=A redetermination of lead(IV) acetate |journal=Acta Crystallographica Section C |volume=50 |issue=11 |year=1994 |pages=1710–1713 |issn=0108-2701 |doi=10.1107/S0108270194006438|doi-access=}}</ref>
 ==Preparation==
-It is typically prepared by treating of [[red lead]] with [[acetic acid]] and [[acetic anhydride]] ({{chem2|Ac2O}}), which absorbs water. The net reaction is shown:<ref>{{cite book |author=J. C. Bailar, Jr. |title=Inorganic Syntheses |series=Inorganic Syntheses |volume=1 |pages=47–49 |year=1939 |chapter=Lead Tetracetate |doi=10.1002/9780470132326.ch17|isbn=9780470132326}}</ref>
+It is typically prepared by treating of [[red lead]] with [[acetic acid]] and [[acetic anhydride]] ({{chem2|Ac2O}}), which absorbs water. The net reaction is shown:<ref>{{cite book |author=J. C. Bailar, Jr. |title=Inorganic Syntheses |series=Inorganic Syntheses |volume=1 |pages=47–49 |year=1939 |chapter=Lead Tetracetate |doi=10.1002/9780470132326.ch17|isbn=978-0-470-13232-6}}</ref><ref>{{cite book|author=M. Baudler|chapter=Lead(IV) Acetate|title=Handbook of Preparative Inorganic Chemistry, 2nd Ed. |editor=G. Brauer|publisher=Academic Press|year=1963|place=NY,NY|volume=2|pages=767}}</ref>
-:<chem>Pb3O4 + 4 Ac2O -> Pb(OAc)4 + 2 Pb(OAc)2</chem>
+:{{chem2|Pb3O4 + 4 Ac2O -> Pb(OAc)4 + 2 Pb(OAc)2}}
-The remaining [[lead(II) acetate]] can be partially oxidized to the tetraacetate:
+The remaining [[lead(II) acetate]] can be partially oxidized to the tetraacetate by Cl<sub>2</sub>, with a [[Lead(II) chloride|PbCl<sub>2</sub>]] by-product:
-:<chem>2 Pb(OAc)2 + Cl2 -> Pb(OAc)4 + PbCl2</chem>
+:{{chem2|2 Pb(OAc)2 + Cl2 -> Pb(OAc)4 + PbCl2}}
 ==Reagent in organic chemistry==
-Lead tetraacetate is a strong [[oxidizing agent]],<ref>{{cite journal |last=J. Zýka |title=Analytical study of the basic properties of lead tetraacetate as oxidizing agent |journal=Pure and Applied Chemistry |year=1966 |volume=13 |issue=4 |pages=569–581 |doi=10.1351/pac196613040569 |s2cid=96821219 |url=http://pac.iupac.org/publications/pac/pdf/1966/pdf/1304x0569.pdf |accessdate=19 December 2013}}</ref> a source of [[acetyloxy]] groups and a general [[reagent]] for the introduction of [[lead]] into [[organolead compound]]s. Some of its many uses in [[organic chemistry]]:
+Lead tetraacetate is a strong [[oxidizing agent]],<ref>{{cite journal |last=J. Zýka |title=Analytical study of the basic properties of lead tetraacetate as oxidizing agent |journal=Pure and Applied Chemistry |year=1966 |volume=13 |issue=4 |pages=569–581 |doi=10.1351/pac196613040569 |s2cid=96821219 |url=http://pac.iupac.org/publications/pac/pdf/1966/pdf/1304x0569.pdf |access-date=19 December 2013}}</ref> a source of [[acetyloxy]] groups, and a general [[reagent]] for the preparation of [[organolead compound]]s. 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 <ref>[[Organic Syntheses]], Vol. 82, p.99 (2005) [http://www.orgsynth.org/orgsyn/prep.asp?prep=v82p0099 Article].
+*[[Acetoxylation]] of benzylic, allylic,<ref>{{cite journal|doi=10.15227/orgsyn.072.0057 |title=(1R,5R)-(+)-Verbenone of High Optical Purity |journal=Organic Syntheses |date=1995 |volume=72 |page=57 }}</ref> and α-oxygen ether C−H bonds, for example the conversion of [[dioxane]] to 2-acetoxy-1,4-dioxane <ref>[[Organic Syntheses]], Vol. 82, p.99 (2005) [http://www.orgsynth.org/orgsyn/prep.asp?prep=v82p0099 Article].
+</ref>
-</ref> and the conversion of [[α-pinene]] to [[verbenone]]<ref>Organic Syntheses, Coll. Vol. 9, p.745 (1998); Vol. 72, p.57 (1995) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv9p0745 Article]</ref>
 * An alternative reagent to [[bromine]] in [[Hofmann rearrangement]]<ref>{{cite journal|author1=Baumgarten, Henry |author2=Smith, Howard |author3=Staklis, Andris |title=Reactions of amines. XVIII. Oxidative rearrangement of amides with lead tetraacetate|journal=The Journal of Organic Chemistry|year=1975|volume=40|issue=24|pages=3554–3561|doi=10.1021/jo00912a019}}</ref>
+* Dehydrogenation of hydrazones and hydrazines, for example that of hexafluoroacetone hydrazone to bis(trifluoromethyl)diazomethane<ref>{{cite journal |doi=10.15227/orgsyn.050.0006 |title=Bis(Trifluoromethyl)Diazomethane |journal=Organic Syntheses |date=1970 |volume=50 |page=6|first1=W. J. |last1=Middleton|first2=D. M. |last2=Gale }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.055.0114 |title=Preparation of N-Aminoaziridines: trans-1-Amino-2,3-diphenylaziridine, 1-Amino-2-phenylaziridine, and 1-Amino-2-phenylaziridinium Acetate |journal=Organic Syntheses |date=1976 |volume=55 |page=114|author=Robert K. Muller, Renato Joos, Dorothee Felix, Jakob Schreiber, Claude Wintner, and A. Eschenmoser }}</ref>
-* Oxidation of [[hydrazone]]s to [[diazo]] compounds, for example that of ''hexafluoroacetone hydrazone'' to ''bis(trifluoromethyl)diazomethane''<ref>Organic Syntheses, Coll. Vol. 6, p.161 (1988); Vol. 50, p.6 (1970) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv6p0161 Article].</ref>
-* [[Aziridine]] formation, for example the reaction of [[phthalimide|''N''-aminophthalimide]] and [[stilbene]]<ref>[[Organic Syntheses]], Coll. Vol. 6, p.56 (1988); Vol. 55, p.114 (1976) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv6p0056 Link]</ref>
 * [[Bond cleavage|Cleavage]] of [[Alpha hydroxy acid|α-hydroxy acids]]<ref>{{cite journal|last1=Ōeda|first1=Haruomi|title=Oxidation of some α-hydroxy-acids with lead tetraacetate|journal=Bulletin of the Chemical Society of Japan|date=1934|volume=9|issue=1|pages=8–14|doi=10.1246/bcsj.9.8|doi-access=free}}</ref> or 1,2-[[diol]]s to their corresponding [[aldehyde]]s or [[ketone]]s, often replacing [[ozonolysis]]; for instance, the oxidation of di-''n''-butyl {{sc|d}}-[[tartrate]] to  ''n''-butyl [[glyoxylate]].<ref>Organic Syntheses, Coll. Vol. 4, p.124 (1963); Vol. 35, p.18 (1955) [http://www.orgsynth.org/orgsyn/prep.asp?prep=cv4p0124 Article].</ref>
 * Reaction with [[alkene]]s to form γ-[[lactone]]s
@@ Line 72: / Line 79: @@
 ==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.
+Lead(IV) acetate is toxic. It is a neurotoxin. It affects the gum tissue, central nervous system, kidneys, blood, and reproductive system.
 ==References==

v t e Lead compounds
Pb(II)	Pb(BiO₃)₂ PbBr₂ Pb(C₅H₅)₂ Pb(C₂H₃O₂)₂ PbC₂O₄ PbC₃₂H₁₆N₈ PbCl₂ Pb(ClO₄)₂ PbCO₃ PbCrO₄ PbF₂ PbHAsO₄ PbI₂ Pb(C ₁₁H ₂₃COO) ₂ Pb(NO₃)₂ Pb(N₃)₂ PbO Pb(OH)₂ PbPo PbP₇ Pb₃(PO₄)₂ PbS Pb(SCN)₂ PbSe PbSO₄ PbSeO₄ PbTe PbTiO₃ PbGeO₃ C ₃₆H ₇₀PbO ₄ PbO2−2 PbC₂ (hypothetical)
Pb(II,IV)	Pb₃O₄
Pb(IV)	Pb(C₂H₃O₂)₄ PbCl₄ PbF₄ PbH₄ PbO₂ PbS₂ plumbate Pb(OH)₄ (hypothetical)