Benziodoxole

The Dess-Martin periodinane ( DMP ) reagent, U,l-tris(acetyloxy)-l,l-dihydro-l,2-benziodoxol-3(l//)-one, has also been used in several complex syntheses for the oxidation of primary or secondary alcohols to aldehydes or ketones, respectively (e.g., M. Nakatsuka, 1990). It is prepared from 2-iodobenzoic add by oxidation with bromic add and acetylation (D.a Dess, 1983). 

CF,C02)2lPh, H2O, CH3CN, 85-99% yield. In the presence of ethylene glycol the dithiane can be converted to a dioxolane (91% yield) or in the presence of methanol to the dimethyl acetal. The reaction conditions are not compatible with primary amides. Thioesters are not affected. A phenylthio ester is stable to these conditions, but amides are not. The hypervalent iodine derivative l-(t-butylperoxy)-l,2-benziodoxol-3(l/f)-one similarly cleaves thioketals."... 

Benziodoxol 1782 can be readily converted by Me3SiCN 18 into HMDSO 7 and 1-cyanobenziodoxol 1783, which oxidizes N,N-dimethylaniline in 96% yield into N-cya-... 

Tetrafluoroammonium hexafluoromanganate, 4384 Tetrafluoroammonium hexafluoronickelate, 4385 Tetrafluoroammonium hexafluoroxenate Tetranitromethane, 0546 Titanium tetraperchlorate, 4170 1,1,1 -Triacetoxy-1,2-benziodoxol-3-one, 3610 Trifluoromethyl hypofluorite, 0353 Trimethylsilyl chlorochromate, 1301 Trioxygen difluoride , 4323 Uranium hexafluoride, 4375 Vanadium(V) oxide, 4866 Vanadium trinitrate oxide, 4763 Vanadyl perchlorate, 4152 Xenon hexafluoride, 4377 Xenon(II) pentafluoroorthoselenate, 4382 Xenon(II) pentafluoroorthotellurate, 4383 Xenon tetrafluoride, 4353 Xenon tetrafluoride oxide, 4346 Xenon tetraoxide, 4863 Xenon trioxide, 4857 Zinc permanganate, 4710... 

The electrochemical transformation of 2-methoxy- and 2-methylphenols to give orthoquinoid cyclohexadienone synthons with the aid of iodanes has been reported [173]. Iodanes (or hyperva-lent iodine [174, 175]) are a large family of reagents [176, 177] and often beneficial as clean and recyclable reagents [178]. The two most often utilized reagents are 2-Iodoxybenzoic (IBX) acid and l,l,l-triacetoxy-l,l-dihydro-l,2-benziodoxol-3(lH)-one (Dess-Martin pe-riodinane, DMP) (see Scheme 7). These... 

A. 1 -Hydroxy-1,2-benziodoxol-3(1 H)-one 1-oxide (1). A 2-L, three-necked, round-bottomed flask, fitted with a mechanical stirrer, condenser, and an immersion thermometer is charged with 80.0 g (0.48 mol) of potassium bromate (KB1O3) and 750 mL of 2.0 M sulfuric acid (Notes 1-3). The resulting clear solution is heated to 60°C in an oil bath and 80.0 g of finely powdered 2-iodobenzoic acid (0.323 mol) is added in... 

Use of higher concentration sulfuric acid ( 2.0 M) than traditionally employed is crucial to allow complete conversion of the 2-iodobenzoic acid to 1.2 In the submitters hands, use of lower concentrations ( 0.5 M) of sulfuric acid at 60°C led to exclusive formation of 1-hydroxy-1,2-benziodoxol-3(1 H)-one. When lower concentrations of sulfuric acid are employed, higher temperatures are required to effect oxidation, as judged by the initiation of bromine evolution. One of the factors leading to the lack of reproducibility in the preparation of 2 results from incomplete conversion to 1. 

Monitoring the reaction by NMR immediately upon dissolution of 1 indicated that the major product was the desired 2 accompanied by a minor amount of what is likely the l(V) monoacetate and a small amount (<5%) of 1-acetoxy-1,2-benziodoxol-3(1H)-one possibly resulting from incomplete oxidation to 1 (see Note 17 for chemical... 

The Dess-Martin periodinane [1,1,1 -triacetoxy-1,1 -dihydro-1,2-benziodoxol-3(1H)-one (2)) is one of several 12-1-5 periodinane species developed by J. C. Martin... 

Iodylbenzoic acid (l-Hydroxy-l,2-benziodoxol-3-one-l-oxide) [64297-64-9] (Acid) [131-62-4] (Iodoxolone)... 

Calcium 2-iodylbenzoate See 1,1,1 -Triacetoxy-1,2-benziodoxol-3-one See other IODINE compounds, organic acids... 

Tetrafluoroammonium hexafluoromanganate, 4378 Tetrafluoroammonium hexafluoronickelate, 4379 Tetrafluoroammonium hexafluoroxenate, 4380 Tetranitromethane, 0543 Titanium tetraperchlorate, 4164 1,1,1 -Triacetoxy-1,2-benziodoxol-3-one, 3604 Trifluoromethyl hypofluorite, 0352 Trimethylsilyl chlorochromate, 1297 Trioxygen difluoride , 4317 Uranium hexafluoride, 4369 Vanadium trinitrate oxide, 4758 Vanadium(V) oxide, 4860 Vanadyl perchlorate, 4146 Xenon hexafluoride, 4371 Xenon tetrafluoride, 4347 Xenon tetrafluoride oxide, 4340 Xenon tetraoxide, 4857 Xenon trioxide, 4851 Xenon(II) pentafluoroorthoselenate, 4376 Xenon(II) pentafluoroorthotellurate, 4377 Zinc permanganate, 4705 ACETYLENIC PEROXIDES ACYL HYPOHALITES ALKYL HYDROPEROXIDES ALKYL TRIALKYLLEAD PEROXIDES AMINIUM IODATES AND PERIODATES AMMINECHROMIUM PEROXOCOMPLEXES BIS (FLUOROOXY)PERHALOALKANES BLEACHING POWDER CHLORITE SALTS... 

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