10.10- bis trifluoroacetoxy

Bis-(trifluoroacetoxy)iodobenzene [2712-78-9] M 430.0, m 112-114 (dec), 120-121 , 124-126". Cryst from warm trifluoroacetic acid and dry over NaOH pellets. Recrystd from Me2CO/pet ether. Melting point depends on heating rate. [Synthesis 445 1975.]... 

An interesting development of this research is the preparation of polymer-supported FITS reagent from bis(trifluoroacetoxy)iodoperfluoroalkanes and Nafion-H [145]. FITS-Nafion reacts with organic substrates that react to usual FITS reagents, but the products of the perfluoroalkylation reaction can be separated easily from the insoluble resin by filtration [145]... 

A synthesis for the enantiomerically pure 535 was developed starting with D-phenylalanine which upon reaction with methyl chloroformate gave 528 whose reaction with methoxylamine afforded 529. Cyclization with bis(trifluoroacetoxy)iodobenzene in presence of trifluoroacetic acid gave the tetrahydroquinoline derivative 530 which was demethoxylated to give 531. Treatment of 531 with either benzyl chloroformate or... 

Oxidation of 5//-dibenz[7>,/]azepine (12) with Fremy s salt [ON(S03K)2] yields a mixture of acridine-9-carbaldehyde (13) and 2//-dibenz[A,/]azepin-2-one (14).215 The dibenzazepin-2-one 14 is also obtained in 46% yield with bis(trifluoroacetoxy)pentafluoroiodobenzene [PhI(OCOCF3)2] in acetonitrile as the oxidant.221... 

The mechanism of oxidation probably involves in most cases the initial formation of a glycol (15-35) or cyclic ester,and then further oxidation as in 19-7. In line with the electrophilic attack on the alkene, triple-bonds are more resistant to oxidation than double bonds. Terminal triple-bond compounds can be cleaved to carboxylic acids (RC=CHRCOOH) with thallium(III) nitrate or with [bis(trifluoroacetoxy)iodo]pentafluorobenzene, that is, C6F5l(OCOCF3)2, among other reagents. 

Interaction to produce 3,5-dimethyl-4-bis(trifluoroacetoxy)iodoisoxazole yields a detonable by-product, believed to be iodine pentaoxide contaminated with organic material. 

Bis (triethylstannyl)acetylene Bis(triethylstannyl) sulphate [57-52-3] Bis(trifluoroacetoxy)dibutylstannane [52112-09-1 ] Bis(trimethylhexyl)dichlorostannane [64011-34-8] Bis(triphenylstannyl) sulphate [3021-41-8]... 

Synthesis of l,3-dihydro-2,2-bis(trifluoroacetoxy)-benzo[c]tellurophenef A mixture of 2,2-diiodo-l,3-dihydrobenzo[c]tellurophene (4.86 g, 10 mmol) and silver trifluoroacetate (4.42 g, 20 mmol) in benzene (200 mL) was stirred at room temperature for 2 h. After filtration, the fdtrate was concentrated to give l,3-dihydro-2,2-bis(trifluoroacetoxy)-benzo[c]tellnrophene (4.17 g, 91%), m. p. 160°C (dec.). 

Oximes also have been reduced to hydroxylamines with bis(trifluoroacetoxy) borane " and photochemically with PhSetf . 

The synthesis of 1,2,5-oxadiazoles is based on cyclization of l,2-dioximes or a-nitrooxime derivatives. The chemistry of dioximes is reviewed by Kotali and Papageorgiou. Thus, reaction of dioximes 270 with 5% aqueous NaOCl in the presence of NaOH in EtOH afforded l,2,5-oxadiazole-2-oxides 271 in good yields (equation 116) . Bromocyan , N2O4/CH2CI2 , bis(trifluoroacetoxy)iodobenzene and Si02 at 150 were also used as reactants in the cyclization of 1,2-dioximes to 1,2,5-oxadiazoles. 

In addition to the aforementioned syntheses of various carbazole-l,4-quinone alkaloids, many formal syntheses for this class of carbazole alkaloids were also reported. These syntheses involve the oxidation of the appropriate 1- or 4-oxygenated-3-methylcarbazoles using Fremy s salt (potassium nitrosodisulfonate), or PCC (pyridinium chlorochromate), or Phl(OCCXI F3)2 [bis(trifluoroacetoxy)iodo]-benzene. Our iron-mediated formal synthesis of murrayaquinone A (107) was achieved starting from murrayafoline A (7) (see Scheme 5.34). Cleavage of the methyl ether in murrayafoline A (7) and subsequent oxidation of the resulting intermediate hydroxycarbazole with Fremy s salt provided murrayaquinone A (107) (574,632) (Scheme 5.113). 

Addition of methyllithium to the lactone 1219, followed by reduction with sodium borohydride in refluxing ethanol, afforded, almost quantitatively, ellipticine (228). Reaction of the compound 1219 with the lithio derivative of formaldehyde diethylmercaptal, and reduction with sodium borohydride in refluxing ethanol, led to the mercaptal 1221. Cleavage of the mercaptal 1221 with bis(trifluoroacetoxy) iodobenzene [Phl(OCOCF3)2] in aqueous acetonitrile gave the 11-formyl derivative, which was reduced with sodium cyanoborohydride (NaBHsCN) to 12-hydroxyellipticine (232) (710,711) (Scheme 5.202). The same group also reported the synthesis of further pyiido[4,3-fc]carbazole derivatives by condensation of 2-substituted indoles with 3-acetylpyridine (712). 

Anunonimn periodate, 4514 Azidoiodoiodonimn hexafluoroantimonate, 4361 [/, /-Bis(trifluoroacetoxy)iodo]benzene, 3239 Boron triiodide, 0150... 

HOFNAHH REARRANGEMENT UNDER MILDLY ACIDIC CONDITIONS USING [I,I-BIS(TRIFLUOROACETOXY)]lODOBENZENE CYCLOBUTYLAW NE HYDROCHLORIDE FROM CYCLOBUTANECARBOXAMIDE (Cyclobutananrine hydrochloride)... 

Although iodine(III) reagents attack double bonds, the rearrangement of the amide group is, at least in some cases, more rapid than electrophilic attack on alkenes. Thus 3-cyclohexene-l-carboxamide rearranges smoothly to the corresponding amine as long as only one equivalent of [1,1-bis(trifluoroacetoxy)iodojbenzene is used. 

Oxathiane 2-oxides aie fonned by the oxidative ring expansion of 2-alkylthio-2-benzylthiolane 1-oxides brought about by [bis(trifluoroacetoxy)iodo]benzene. That the reaction is only successful with the (lR )-diastereoisomeis is attributed to chelation between the nucleophilic S and O atoms and the hypervalent iodine <99EJ0943>. A diazo-mediated thiolane ring expansion is the key step in a synthesis of the acenaphtho-[U-b][l,4]oxathiine system <99JCS(P2)755>. 

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