Organic Polyvalent Iodine Compounds

A series of compounds possessing polyvalent iodine groups was prepared from onitroiodobenzene. Single crystal X-ray investigation revealed a strong interaction between iodine atom and one of the oxygen atoms of the nitro group. This interaction is strongest in trifluoroacetate of hydroxy(o-nitrophenyl)iodonium salt, which is formed from an iodosylarene and an acid being the first example of this new class of compounds. These compounds are also characterized by NMR-spectroscopy.

Section: Introductionmentioning

confidence: 99%

Hypervalent iodine compounds derived from o-nitroiodobenzene and related compounds: syntheses and structures

Nikiforov¹,

Karavan²,

Miltsov³

et al. 2003

“…[1][2][3][4][5][6][7] In particular, both iodine(III) and iodine(V) compounds of the IL 3 and IL 5 types in which L is a monovalent electronegative ligand (i.e., λ 3 -iodanes and λ 5 -iodanes) can advantageously replace heavy metal-based reagents as inexpensive, non-toxic and yet efficient oxidants. The λ 3 -iodanes most commonly used today in oxidation reactions, including oxygenation reactions such as acetoxylation, methoxylation, hydroxylation, tosyloxylation and epoxidation, are (diacetoxyiodo)benzene (DIB), [bis(trifluoroacetoxy)iodo]benzene (BTI), [hydroxy(tosyloxy)iodo]benzene (HTI or "Koser's reagent") 8 and iodosylbenzene (PhIO, IOB).…”

Section: Introductionmentioning

confidence: 99%

Iodane-mediated and electrochemical oxidative transformations of 2-methoxy- and 2-methylphenols

Quideau¹,

Pouységu²,

Deffieux³

et al. 2003

A series of 2-methoxy and 2-methylphenols have been submitted to oxygenative oxidation reactions using (1) the λ 3 -iodane DIB, (2) a non-explosive and non-moisture sensitive version of the λ 5 -iodane IBX, named SIBX for Stabilized IBX, and (3) anodic oxidation with the aim of identifying the best reaction conditions for preparing orthoquinonoid cyclohexadienone synthons. Both the use of DIB and anodic oxidation appeared equally valuable for making orthoquinone dimethyl ketals, but the λ 3 -and λ 5-iodane reagents are more appropriate to induce ortho-oxygenation of 2-methylphenols. In particular, SIBX emerged as a useful reagent for mediating ortho-hydroxylation into dimerizing orthoquinols, a tactic that can be applied to the synthesis of natural bis(monoterpenoids) such as aquaticol.

“…[1][2][3][4][5][6] They can be used for a wide range of chemical transformations, especially as reagents for oxidations. [7][8][9][10][11] For these purposes, iodinanes like (diacetoxyiodo)-benzene,…”

Section: Introductionmentioning

confidence: 99%

First synthesis and oxidative properties of polymer-supported IBX

Mülbaier¹,

Giannis²

2003

A polymer-supported analogue of the IBX-reagent (1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide) has been synthesized. Synthesis and oxidative properties of this new and efficient reagent are described. With this reagent is it now possible to oxidize alcohols selectively to the corresponding ketones and aldehydes. Over oxidation to carboxylic acids has not been observed. This new reagent combines the advantages of polymer-supported reagents with those of the IBX reagent.