Manganese(III) acetate

Manganese Triacetate

200px
Names
IUPAC name Manganese triacetate
Other names Manganese triacetate dihydrate; Manganese(III) acetate dihydrate
Identifiers
CAS Number	19513-05-4 (dihydrate) Y[scifinder] 26935-72-8 (anhydrous) N
ChemSpider	141084 Y
Jmol 3D model	Interactive image
PubChem	160554
InChI InChI=1S/3C2H4O2.Mn/c3*1-2(3)4;/h3*1H3,(H,3,4);/q;;;+3/p-3 Y Key: AHSBSUVHXDIAEY-UHFFFAOYSA-K Y InChI=1/3C2H4O2.Mn/c3*1-2(3)4;/h3*1H3,(H,3,4);/q;;;+3/p-3 Key: AHSBSUVHXDIAEY-DFZHHIFOAL
SMILES [Mn+3].O=C([O-])C.[O-]C(=O)C.[O-]C(=O)C
Properties
Chemical formula	C6H9MnO6•2H2O
Molar mass	268.13 g/mol (dihydrate)
Appearance	Brown powder
Density	1.049 g cm−3, liquid; 1.266 g cm−3, solid
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

Manganese(III) acetate is an inorganic compound that is used as an oxidizing agent in organic synthesis and materials science. Like the analogous acetates of iron and chromium, it is an oxygen-centered coordination complex containing three manganese atoms bridged by acetate units. The anhydrous form of this compound crystallizes as a linear coordination polymer, with an additional acetic acid molecule bridging between manganese atoms on consecutive three-manganese clusters. The chemical is therefore not a simple metal acetate ionic compound nor does the actual structure of it reflect the simple "Mn(OAc)₃" chemical formula that is commonly given. It is usually used as the dihydrate, though the anhydrous form is also used in some situations. The dihydrate is prepared by reacting potassium permanganate and manganese(II) acetate in acetic acid; addition of acetic anhydride to the reaction produces the anhydrous form. It is also synthesized by electrochemical method starting from Mn(OAc)₂.

Mangese triacetate has been used as a single electron oxidant. It can oxidize alkenes via addition of acetic acid to form lactones.

300px

This process is thought to proceed via the formation of a •CH₂CO₂H radical intermediate, which then reacts with the alkene, followed by additional oxidation steps and finally ring closure. When the alkene is not symmetric, the major product depends on the nature of the alkene, and is consistent with initial formation of the more stable radical (among the two carbons of the alkene) followed by ring closure onto the more stable conformation of the intermediate.

When reacted with enones, the carbon on the other side of the carbonyl reacts rather than the alkene portion, leading to α'-acetoxy enones. In this process, the carbon next to the carbonyl is oxidized by the manganese, followed by transfer of acetate from the manganese to it.

It can similarly oxidize β-ketoesters at the α carbon, and this intermediate can react with various other structures, including halides and alkenes (see: manganese-mediated coupling reactions). One extension of this idea is the cyclization of the ketoester portion of the molecule with an alkene elsewhere in the same structure.

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