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Hypervalent Iodine Compounds [Synthetic Reagents]

 Iodine is atomic number 53, in the 5th period, Group 17, halogens of the periodic table. Iodine is a large-sized halogen element, easily polarizable, and low in electronegativity. It forms hypervalent organoiodanes beyond the octet theory by readily extending its valence. For example, hypervalent organoiodane with three ligands is a 10-I-3 type compound as shown in the figure. The central iodine atom forms a plane with two lone pairs and one σ-bond, and furthermore, this iodine atom coordinates two ligands with larger electronegativity in an apical position orthogonal to the plane resulting in the formation of a linear three center-four electron bond. The I-L bond in the apical position is weaker and longer than the covalent bond. For example, the I-O bond length in PhI(OAc)2 is longer than the sum of their covalent bond radii (1.99 Å) and these bond lengths have a range of 2.15~2.16 Å.
 The stability and reactivity of hypervalent organoiodanes exhibit a greater dependence on the character of hypervalent bonds in the apical position. The hypervalent bonds in the apical position are easily cleaved, and the cleavage causes trivalent iodines with 10 electrons to be reduced to monovalent iodines of a more stable octet structure. For this reason, it exhibits good elimination and oxidation rate and finds application in organic syntheses.1~3) (Diacetoxyiodo)benzene, the most typical trivalent iodine compounds, which is attempted to support the polymers. For example, Togo and coworkers have demonstrated several oxidative functional group conversion reactions using poly[4-(diacetoxyiodo)styrene](1).4) After reaction, this polymer-supported reagent can be recovered by filtration and reused after re-oxidation with peracetic acid. Therefore, it is expected to be used as environmentallyfriendly chemical conversion reagent in the near future.
Many hypervalent organoiodanes may decompose violently when exposed to heat, shock, and friction, etc. Sufficient safety measures, such as usage of safety shield, wearing of protective equipment, and extreme caution should be taken, when using this compound, from the opening up to the disposal of the reagents.
A2678
1-Acetoxy-5-bromo-1,2-benziodoxol-3(1H)-one
B1175
[Bis(trifluoroacetoxy)iodo]benzene
B1616
[Bis(trifluoroacetoxy)iodo]pentafluorobenzene
B2359
Bis(2,4,6-trimethylpyridine)iodonium Hexafluorophosphate
B2380
Bis(4-tert-butylphenyl)iodonium Hexafluorophosphate
B2539
Bis(pyridine)iodonium Tetrafluoroborate
B5259
Bis(4-bromophenyl)iodonium Trifluoromethanesulfonate
B5260
Bis(2,4,6-trimethylphenyl)iodonium Trifluoromethanesulfonate
B5269
[4-(Bromomethyl)phenyl](2,4,6-trimethoxyphenyl)iodonium p-Toluenesulfonate
B5276
Bis(4-fluorophenyl)iodonium Trifluoromethanesulfonate
B5277
(3-Bromophenyl)(mesityl)iodonium Trifluoromethanesulfonate
B5405
[Bis(tert-butylcarbonyloxy)iodo]benzene
B5573
4-Biphenylyl(2,4,6-trimethoxyphenyl)iodonium Trifluoromethanesulfonate
B5956
Bis[4-(tert-butyl)phenyl]iodonium Tetra(nonafluoro-tert-butoxy)aluminate
D2045
Dess-Martin Periodinane
D2238
Diphenyliodonium Hexafluorophosphate
D2243
Diphenyliodonium Perchlorate
D2248
Diphenyliodonium Hexafluoroarsenate
D2253
Diphenyliodonium Trifluoromethanesulfonate
D2356
Diphenyliodonium Chloride
D2357
Diphenyliodonium Nitrate
D2372
Diphenyliodonium Bromide
D2373
Diphenyliodonium Iodide
D2503
Diphenyliodonium-2-carboxylate Monohydrate
D4477
Dess-Martin Periodinane (8-12% in Dichloromethane)
D5145
(3,5-Dichlorophenyl)(2,4,6-trimethoxyphenyl)iodonium p-Toluenesulfonate
E0467
Ethynyl(phenyl)iodonium Tetrafluoroborate [Ethynylating Reagent]
F0957
1-Fluoro-3,3-dimethyl-1,2-benziodoxole
F1110
(5-Fluoro-2-nitrophenyl)(2,4,6-trimethoxyphenyl)iodonium p-Toluenesulfonate
F1111
[4-Fluoro-3-(trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)iodonium p-Toluenesulfonate
I0072
Iodosobenzene
I0073
2-Iodosobenzoic Acid
I0330
Iodobenzene Diacetate
I0479
Iodomesitylene Diacetate
I0591
4-Isopropyl-4'-methyldiphenyliodonium Tetrakis(pentafluorophenyl)borate
I0791
2-Iodoxybenzoic Acid (stabilized with Benzoic Acid + Isophthalic Acid)
I0865
Iodosodilactone
I1126
1-(1H-Indol-3-yl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one
M2907
(2-Methylphenyl)(2,4,6-trimethylphenyl)iodonium Trifluoromethanesulfonate
M2908
(3-Methylphenyl)(2,4,6-trimethylphenyl)iodonium Trifluoromethanesulfonate
M2909
(4-Methylphenyl)(2,4,6-trimethylphenyl)iodonium Trifluoromethanesulfonate
N1066
(4-Nitrophenyl)(phenyl)iodonium Trifluoromethanesulfonate
P0077
Trisodium Paraperiodate
P1015
[Hydroxy(tosyloxy)iodo]benzene
P1080
(Perfluorohexyl)phenyliodonium Trifluoromethanesulfonate
P1081
(Perfluoro-n-octyl)phenyliodonium Trifluoromethanesulfonate
P1082
(Perfluoropropyl)phenyliodonium Trifluoromethanesulfonate
P1239
Trimethylsilylethynyl(phenyl)iodonium Tetrafluoroborate
P1298
[Hydroxy(methanesulfonyloxy)iodo]benzene
P1415
Poly[4-(diacetoxyiodo)styrene]
P1620
Phenyl[2-(trimethylsilyl)phenyl]iodonium Trifluoromethanesulfonate
P2097
Phenyl[4-(trimethylsilyl)thiophen-3-yl]iodonium Trifluoromethanesulfonate
P2143
Benzoyl(phenyliodonio)(trifluoromethanesulfonyl)methanide
P2412
Phenyl(2,4,6-trimethoxyphenyl)iodonium p-Toluenesulfonate
P2413
Phenyl[3-(trifluoromethyl)phenyl]iodonium Trifluoromethanesulfonate
T2624
1-Trifluoromethyl-3,3-dimethyl-1,2-benziodoxole
T3014
1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one (contains 60% Diatomaceous earth)
T3039
1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one
T3272
1-[(Trimethylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one
T3445
[3-(Trifluoromethyl)phenyl](2,4,6-trimethylphenyl)iodonium Trifluoromethanesulfonate
T3446
[4-(Trifluoromethyl)phenyl](2,4,6-trimethylphenyl)iodonium Trifluoromethanesulfonate
T3590
1-[2-(Triisopropylsilyl)ethynyl]-3,3-bis(trifluoromethyl)-1,2-benziodoxole
T3622
[(4-Trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)iodonium p-Toluenesulfonate

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