- Applying the Power of Reticular Chemistry to Finding the Missing alb-MOF Platform Based on the (6,12)-Coordinated Edge-Transitive Net
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Highly connected and edge-transitive nets are of prime importance in crystal chemistry and are regarded as ideal blueprints for the rational design and construction of metal-organic frameworks (MOFs). We report the design and synthesis of highly connected
- Chen, Zhijie,Weseliński, ?ukasz J.,Adil, Karim,Belmabkhout, Youssef,Shkurenko, Aleksander,Jiang, Hao,Bhatt, Prashant M.,Guillerm, Vincent,Dauzon, Emilie,Xue, Dong-Xu,O’Keeffe, Michael,Eddaoudi, Mohamed
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- Covalent Organic Helical Cages as Sandwich Compound Containers
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A covalent organic helical cage (COHC) with D3symmetry bearing two 1,3,5-trimethylphenyl cores and six di-tert-butyldiethynylallene moieties was synthesized and fully characterized. This molecular structure cage, unlike a previously reported on
- Míguez-Lago, Sandra,Cid, M. Magdalena,Alonso-Gómez, J. Lorenzo
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- A new stable porous Pr-organic framework constructed by multi-iodine-substituted aromatic polycarboxylates: Synthesis, characterization, and selective adsorption of dyes
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Poly[tris(dimethylformamide)(μ3-2,4,6-triiodol-1,3,5-benzene tricarboxylic acid)-praseodymium (III)] {Pr(TIBTC)(DMF)3}n (1) (H3TIBTC = 2,4,6-triiodo-1,3,5-benzene tricarboxylic acid) was synthesized by the reaction of Pr(NO3)3·6H2O and H3TIBTC at 85°C in a pyrex vial. 1 was characterized by elemental analysis, IR, UV–vis, TGA, PXRD, and atomic force microscopy analytical means. Each of the central Pr ions and the three carboxyl groups from the same ligand constitute a SBU, which is then joined by a carboxyl group to form a building block. In order to further explore the functional properties of 1, we used this compound for adsorption experiments. It is found that 1 can effectively adsorb anionic dyes in aqueous solutions. In particular, there is a good adsorption efficiency for coomassie brilliant blue R-250. Therefore, 1 shows good prospects for selective adsorption of anionic dyes from wastewater solution.
- Sun, Ying,Bai, Feng Ying,Min Wang, Xue,Wang, Yu,Xian Sun, Li,Heng Xing, Yong
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- A family of functional Ln-organic framework constructed by iodine-substituted aromatic polycarboxylic acid for turn-off sensing of UO22+
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With the rapid development of nuclear energy, one of the main constraints restricting the development of nuclear energy is the long-term safe disposal of strong uranium waste. Here it is a great significance that we use four new synthetic Ln (III)-based coordination polymers to test the uranium solution. In this study, four three-dimensional coordination polymers 1–4 (CPs-(1–4); Ln?=?Eu, Gd, Sm, Nd) were successfully synthesized through 1:1 complexation of Ln (NO3)3·6H2O with poly-carboxylic acid ligand H3TIBTC (2,4,6-Triiodo-1,3,5-benzene tricarboxylic acid) which contains substituents of the carboxylic acid group and halogen atom, respectively. Based on the ligand being excellent fluorescent properties in the solution, it prompted us to further study the fluorescence properties of the coordination polymers. Experimental results show that the coordination polymers are favorable materials for the simultaneous selective detection uranium solution from water, being potentially useful in monitoring water quality and treating uranium-wastewater.
- Wang, Yu,Xing, Shang-Hua,Zhang, Xu,Liu, Chun-Hong,Li, Bing,Bai, Feng-Ying,Xing, Yong-Heng,Sun, Li-Xian
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- Water-Stable In(III)-Based Metal-Organic Frameworks with Rod-Shaped Secondary Building Units: Single-Crystal to Single-Crystal Transformation and Selective Sorption of C2H2 over CO2 and CH4
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Three new water-stable In(III)-based metal-organic frameworks, namely, [In3(TTTA)2(OH)3(H2O)]·(DMA)3 (BUT-70, DMA = N,N-dimethylacetamide), [In3(TTTA)2(CH3O)3/su
- Guo, Zhen-Ji,Yu, Jiamei,Zhang, Yong-Zheng,Zhang, Jian,Chen, Ya,Wu, Yufeng,Xie, Lin-Hua,Li, Jian-Rong
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- A rigid C3v-symmetrical host for saccharide recognition: 1,3,5-tris(2-hydroxyaryl)-2,4,6-trimethylbenzenes
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(Chemical Equation Presented) A rigid C3v-symmetrical host molecule, syn-1,3,5-tris(2-hydroxy-5-pentylphenyl)-2,4,6-trimethylbenzene, was readily obtained via Suzuki coupling and thermal atropisomerization. The host molecule effectively associa
- Abe, Hajime,Aoyagi, Yoshinobu,Inouye, Masahiko
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- 1,3,5-triiodo-2,4,6-trimethylbenzene at 293 K
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In the structure of triiodomesitylene (1,3,5-triiodo-2,4,6-trimethylbenzene), C9H9I3, at 293 K, the benzene ring is found to be significantly distorted from ideal D6h symmetry; the average endocyclic angles faci
- Boudjada,Hernandez,Meinnel,Mani,Paulus
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- Aggregation-Induced Emission of Triphenyl-Substituted Tristyrylbenzenes
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The synthesis, properties and X-ray single-crystal structures of two regioisomeric triphenyl tristyrylbenzenes are reported. Both C3v and Cs derivatives display aggregation-induced emission (AIE) behavior. Regioisomerism impacts the
- Zhang, Hao,Rominger, Frank,Bunz, Uwe H. F.,Freudenberg, Jan
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- Methyl-restricted rotor rotation on the stator produces high-efficiency fluorescence emission: A new strategy to achieve aggregation-induced emission
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At present, we have realized that the aggregation-induced emission (AIE) achieves the purpose of fluorescence enhancement by restricting rotations to reduce intermolecular or intramolecular energy loss. Based on this idea, we synthesized a novel fluorene-
- Yang, Haicheng,Zhou, Xinyue,Hui, Tianqi,Han, Yingying,Jiang, Xiaonan,Yan, Jie
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- Polyiodine-Modified 1,3,5-Benzenetricarboxylic Acid Framework Zn(II)/Cd(II) Complexes as Highly Selective Fluorescence Sensors for Thiamine Hydrochloride, NACs, and Fe3+/Zn2+
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Four new complexes, [Zn(TIBTC)(DMA)]·[NH2(CH3)2] (1), [Cd(TIBTC)(H2O)]·[NH2(CH3)2]·DMA (2), [Cd2(TIBTC)(2,2′-bipy)2(HCOO)] (3), and [Cd2(DIBTC)(2,2′-bipy)2(HCOO)] (4) (H3TIBTC = 2,4,6-triiodo-1,3,5-benzenetricarboxylic acid, H3DIBTC = 2,4-diiodo-1,3,5-benzenetricarboxylic acid, 2,2′-bipy = 2,2′-bipyridine, and DMA = dimethylacetamide), were successfully synthesized and characterized by elemental analysis, powder X-ray diffraction, infrared spectroscopy, ultraviolet-visible spectroscopy, and thermogravimetric analysis. Complexes 1 and 2 are three-dimensional supramolecular network structures, while complex 4 has a two-dimensional network structure. We preliminarily studied the fluorescence properties of the complexes and found that complexes 1-3 can detect thiamine hydrochloride, NACs, and Fe3+/Zn2+ with high sensitivity and selectivity.
- Bai, Feng-Ying,Guan, Qing-Lin,Liu, Chun-Hong,Sun, Li-Xian,Xing, Yong-Heng,Yang, Xiao-Dong
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- MULTICYCLIC PEPTIDES AND METHODS FOR THEIR PREPARATION
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The invention relates to methods for preparing a compound comprising a peptide attached to a molecular scaffold whereby multiple peptide loops are formed, to compounds that can be obtained with such methods and uses thereof.
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Page/Page column 67; 68
(2018/06/30)
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- Modulator-Controlled Synthesis of Microporous STA-26, an Interpenetrated 8,3-Connected Zirconium MOF with the the-i Topology, and its Reversible Lattice Shift
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A fully interpenetrated 8,3-connected zirconium MOF with the the-i topology type, STA-26 (St Andrews porous material-26), has been prepared using the 4,4′,4“-(2,4,6-trimethylbenzene-1,3,5-triyl)tribenzoate (TMTB) tritopic linker with formic acid as a modulating agent. In the as-prepared form STA-26 possesses Im (Formula presented.) m symmetry compared with the Pm (Formula presented.) m symmetry of the non-interpenetrated analogue, NU-1200, prepared using benzoic acid as a modulator. Upon removal of residual solvent there is a shift between the interpenetrating lattices and a resultant symmetry change to Cmcm which is fully reversible. This is observed by X-ray diffraction and 13C MAS NMR is also found to be remarkably sensitive to the structural transition. Furthermore, heating STA-26(Zr) in vacuum dehydroxylates the Zr6 nodes leaving coordinatively unsaturated Zr4+ sites, as shown by IR spectroscopy using CO and CD3CN as probe molecules. Nitrogen adsorption at 77 K together with grand canonical Monte Carlo simulations confirms a microporous, fully interpenetrated, structure with pore volume 0.53 cm3 g?1 while CO2 adsorption at 196 K reaches 300 cm3 STP g?1 at 1 bar. While the pore volume is smaller than that of its non-interpenetrated mesoporous analogue, interpenetration makes the structure more stable to moisture adsorption and introduces shape selectivity in adsorption.
- Bumstead, Alice M.,Cordes, David B.,Dawson, Daniel M.,Chakarova, Kristina K.,Mihaylov, Mihail Y.,Hobday, Claire L.,Düren, Tina,Hadjiivanov, Konstantin I.,Slawin, Alexandra M. Z.,Ashbrook, Sharon E.,Prasad, Ram R. R.,Wright, Paul A.
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supporting information
p. 6115 - 6126
(2018/03/27)
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- Highly Stable Zr(IV)-Based Metal-Organic Frameworks for the Detection and Removal of Antibiotics and Organic Explosives in Water
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Antibiotics and organic explosives are among the main organic pollutants in wastewater; their detection and removal are quite important but challenging. As a new class of porous materials, metal-organic frameworks (MOFs) are considered as a promising platform for the sensing and adsorption applications. In this work, guided by a topological design approach, two stable isostructural Zr(IV)-based MOFs, Zr6O4(OH)8(H2O)4(CTTA)8/3 (BUT-12, H3CTTA = 5′-(4-carboxyphenyl)-2′,4′,6′-trimethyl-[1,1′:3′,1″-terphenyl]-4,4″-dicarboxylic acid) and Zr6O4(OH)8(H2O)4(TTNA)8/3 (BUT-13, H3TTNA = 6,6′,6″-(2,4,6-trimethylbenzene-1,3,5-triyl)tris(2-naphthoic acid)) with the the-a topological structure constructed by D4h 8-connected Zr6 clusters and D3h 3-connected linkers were designed and synthesized. The two MOFs are highly porous with the Brunauer-Emmett-Teller surface area of 3387 and 3948 m2 g-1, respectively. Particularly, BUT-13 features one of the most porous water-stable MOFs reported so far. Interestingly, these MOFs represent excellent fluorescent properties, which can be efficiently quenched by trace amounts of nitrofurazone (NZF) and nitrofurantoin (NFT) antibiotics as well as 2,4,6-trinitrophenol (TNP) and 4-nitrophenol (4-NP) organic explosives in water solution. They are responsive to NZF and TNP at parts per billion (ppb) levels, which are among the best performing luminescent MOF-based sensing materials. Simultaneously, both MOFs also display high adsorption abilities toward these organic molecules. It was demonstrated that the adsorption plays an important role in the preconcentration of analytes, which can further increase the fluorescent quenching efficiency. These results indicate that BUT-12 and -13 are favorable materials for the simultaneous selective detection and removal of specific antibiotics and organic explosives from water, being potentially useful in monitoring water quality and treating wastewater.
- Wang, Bin,Lv, Xiu-Liang,Feng, Dawei,Xie, Lin-Hua,Zhang, Jian,Li, Ming,Xie, Yabo,Li, Jian-Rong,Zhou, Hong-Cai
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supporting information
p. 6204 - 6216
(2016/06/09)
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- Modular syntheses of star-shaped pyridine, bipyridine, and terpyridine derivatives by employing sonogashira reactions
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A simple and flexible synthesis for a series of star-shaped pyridine, bipyridine, and terpyridine derivatives is reported by using a modular approach that combines the use of a ligand, spacer, and core unit. A fairly efficient method to prepare 4′-nonafloxy-functionalized terpyridine derivatives is described. The building blocks that contain the functionalized pyridine, bipyridine, or terpyridine derivatives were linked to different C3-symmetrical core units. In most cases, Sonogashira reactions were employed in the crucial final steps of the synthesis. A star-shaped dodecafluorinated compound was also prepared in a straightforward fashion. A simple procedure for the preparation of partially silylated 1,3,5-triethynylbenzene derivatives is presented, which provides an approach to C2-symmetrical star-shaped compounds that have only one terpyridine and two terphenyl units as "dummy" ligands. The absorption and emission spectra of the fully conjugated C3-symmetrical pyridine derivatives were systematically investigated, and fairly large Stokes shifts were observed.
- Trawny, Daniel,Kunz, Valentin,Reissig, Hans-Ulrich
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supporting information
p. 6295 - 6302
(2015/03/30)
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- Desulfonyloxyiodination of arenesulfonic acids with mCPBA and molecular iodine
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Treatment of p-alkylbenzenesulfonic acids with mCPBA and molecular iodine gave p-alkyliodobenzenes in good to moderate yields via electrophilic ipso-substitution by the iodonium species (I+) formed. This desulfonyloxyiodination was promoted by the addition of a catalytic amount of iodoarenes, such as o-iodobenzoic acid. The same treatment of dimethylbenzenesulfonic acids and trimethylbenzenesulfonic acids with mCPBA and molecular iodine proceeded smoothly both in the absence and in the presence of o-iodobenzoic acid to provide the corresponding monoiodo-dimethylbenzene and diiodo-dimethylbenzene, and diiodo-trimethylbenzene and triiodo- trimethylbenzene, in good to moderate yields, respectively. On the other hand, the same desulfonyloxyiodination of benzenesulfonic acid and p-chlorobenzenesulfonic acid with mCPBA and molecular iodine proceeded only in the presence of o-iodobenzoic acid to generate iodobenzene and p-chloroiodobenzene, respectively, in moderate yields.
- Suzuki, Yuhsuke,Ishiwata, Yoshihide,Moriyama, Katsuhiko,Togo, Hideo
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experimental part
p. 5950 - 5953
(2010/11/21)
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- 1,3-Diiodo-5,5-dimethylhydantoin-An efficient reagent for iodination of aromatic compounds
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1,3-Diiodo-5,5-dimethylhydantoin in organic solvents successfully iodinates alkylbenzenes, aromatic amines, and phenyl ethers. The reactivity of electrophilic iodine is controlled by acidity of the medium. Superelectrophilic iodine generated upon dissolution of 1,3-diiodo-5,5-dimethylhydantoin in sulfuric acid readily reacts with electron-deficient arenes at 0 to 20°C with formation of the corresponding iodo derivatives in good yields. The structure of electrophilic iodine species generated from 1,3-diiodo-5,5- dimethylhydantoin in sulfuric acid is discussed.
- Chaikovskii,Filimonov,Funk,Skorokhodov,Ogorodnikov
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p. 1291 - 1296
(2008/03/27)
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- Selective and effective iodination of alkyl-substituted benzenes with elemental iodine activated by Selectfluor F-TEDA-BF4
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Selective direct introduction of an iodine atom into alkyl-substituted benzene derivatives was effectively achieved by reaction of target molecules with elemental iodine in the presence of 1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF4). The number of iodine atoms introduced could be modulated by the molar ratio between substrate, iodine and F-TEDA-BF4.
- Stavber, Stojan,Kralj, Petra,Zupan, Marko
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p. 598 - 600
(2007/10/03)
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- 2,4,6,8-tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione as a mild and convenient reagent for iodination of aromatic compounds
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2,4,6,8-Tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (tetraiodoglycoluril) is a convenient reagent for preparative iodination of benzene, alkylbenzenes, polycyclic hydrocarbons, aromatic amines, and phenol ethers in organic solvents under mild conditions.
- Chaikovski,Filimonov,Yagovkin,Ogorodnikov
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p. 2411 - 2415
(2007/10/03)
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- Iodinated x-ray contrast media
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The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula C6R6wherein three non-adjacent R groups are iodine and the remaining R groups are non-ionic, hydrophilic moieties, said compou
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- 1,3,5-Trialkyl-2,4,6-triiodobenzenes: Novel x-ray contrast agents for gastrointestinal imaging
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Examination of the gastrointestinal (GI) tract has been performed for decades using barium sulfate. Although this agent has many recognized limitations including extreme radiopacity, poor intrinsic affinity for the GI mucosa, and very high density, no alternative contrast agents have emerged which produce comparable or better contrast visualization. In fact, the various techniques of the GI radiologic examination (i.e., single contrast, double contrast, biphasic) were developed to compensate for its limitations. Each of these techniques requires complex patient manipulation to achieve adequate mucosal coating or compression to overcome the marked radiopacity of barium sulfate in order to obtain a diagnostically useful examination. A series of novel radiopaque oils, the 1,3,5-trialkyl-2,4,6-triiodobenzenes, was designed to improve the efficacy, stability, and safety of barium formulations. These substances were prepared in two steps from 1,3,5- trichlorobenzene. Compound 17 (1,3,5-tri-n-hexyl-2,4,6-triiodobenzene), formulated as an oil-in-water emulsion, was found to be well-tolerated in rodents (mice, hamsters, rats) following acute oral and/or intraperitoneal administrations at 4 times the anticipated human clinical dose. No metabolism of 17 was detected in rat, hamster, dog, monkey, or human hepatic microsomes, suggesting the lack of oral toxicity was a consequence of poor absorption. In imaging experiments in dogs, emulsions of 17 have demonstrated excellent mucosal coating and improved radiodensity relative to barium sulfate suspensions. On the basis of the preliminary imaging and toxicity data, compound 17 was selected as a potential development candidate.
- Estep, Kimberly G.,Josef, Kurt A.,Bacon, Edward R.,Illig, Carl R.,Toner, John L.,Mishra, Dinesh,Blazak, William F.,Miller, Dennis M.,Johnson, David K.,Allen, Jack M.,Spencer, Andy,Wilson, Susan A.
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p. 1940 - 1948
(2007/10/03)
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- Improved, Acid-catalyzed Iodinating Procedures for Activated Aromatics with (Diacetoxyiodo)benzene as the Oxidant
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Improved procedures for the oxidative, acid-catalyzed iodination of benzene, iodobenzene and several activated aromatics are presented to give mono-, di-, or triiodinated products in 40-82 percent yields. The reactions proceeded at room temperature in the anhydrous systems: arene or hetarene/diiodine/(diacetoxyiodo)benzene (2)/glacial acetic acid/acetic anhydride, acidified with catalytic amounts of concd. (98 percent) H2SO4. Within at most 15 minutes the iodine coloration faded; the following workups are explained. A similar treatment with dibromine gave tribromomesitylene (65 percent), dibromodurene (62 percent), and 2,7-dibromofluoren-9-one (73 percent). A review on the aromatic halogenation reactions with organic trivalent iodine reagents as the oxidants is presented below.
- Kryska, Anna,Skulski, Lech
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p. 2501 - 2517
(2007/10/03)
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- Contrast media
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The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula I STR1 (wherein n is 0 or 1, and where n is 1 each C6 R5 moeity may be the same or different; each group R is a hydrogen atom,
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- Contrast media
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The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula I STR1 (wherein n is 0 or 1, and where n is 1 each C6 R5 moeity may be the same or different; each group R is a hydrogen atom,
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- Synthetic use of poly[4-(diacetoxyiodo)styrene] for organic reactions
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Poly[4-(diacetoxyiodo)styrene] is sufficiently reactive for the iodination of aromatics, the oxidative 1,2-aryl migration of alkyl aryl ketones, the α-hydroxylation of ketones, and the oxidation of hydroquinones and sulfides similarly to (diacetoxyiodo)benzene. Here, those reactions with poly[4-(diacetoxyiodo)styrene] are very useful because of the simple operation; thus, filtration gives the crude products and recovered poly(4- iodostyrene), and then poly[4-(diacetoxyiodo)-styrene] can be regenerated by oxidation of the recovered poly(4-iodostyrene), which are reused for the same reactions.
- Togo, Hideo,Abe, Seiichiro,Nogami, Genki,Yokohama, Masataka
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p. 2351 - 2356
(2007/10/03)
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- Synthesis of organometallic dendrimers with a backbone composed of platinum-acetylide units
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Novel organometallic dendrimers containing platinum-acetylide units in the main chain have been synthesized up to a henicosanuclear complex (12) using triethynylmesitylene (4) as a bridging ligand. The molecular structure of trinuclear complex (5b), which
- Ohshiro, Nobuaki,Takei, Fumie,Onitsuka, Kiyotaka,Takahashi, Shigetoshi
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p. 195 - 202
(2007/10/03)
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- Synthetic application of poly[styrene(iodoso diacetate)]
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Poly[styrene(iodoso diacetate)] is sufficiently reactive to effect the iodination of aromatics and oxidative 1,2-aryl migration of alkyl aryl ketones as (diacetoxyiodo)benzene, and can be regenerated and reused for the same reactions.
- Togo, Hideo,Nogami, Genki,Yokoyama, Masataka
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p. 534 - 536
(2007/10/03)
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- Synthesis of a novel organometallic dendrimer with a backbone composed of platinum-acetylide units
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Novel organometallic dendrimers containing platinum-acetylide units in the main chain have been synthesized using 1,3,5-triethyny1-2,4,6-trimethylbenzene (4) as a bridging ligand up to a nonanuclear complex (8).
- Ohshiro, Nobuaki,Takei, Fumie,Onitsuka, Kiyotaka,Takahashi, Shigetoshi
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p. 871 - 872
(2007/10/03)
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- Polyiodination on benzene at room temperature. A regioselective synthesis of derivatives
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Reaction of IPy2BF4 with benzene and CF3SO3H in CH2Cl2 gives regioselectively polyiodinated compounds at room temperature, providing a definitely easy synthetic entry to those rarely accessible benzene derivatives.
- Barluenga,Gonzalez,Garcia-Martin,Campos
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p. 3893 - 3896
(2007/10/02)
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- Steric and electron-withdrawing effects of substituents governing chemical stability and catalytic activity of Mn(III)-tetraarylporphyrins in HOCl/ClO- alkene epoxidations
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Mn(III)-tetrakis(2,4,6-trimethyl-3,5-dihalogenophenyl)porphyrins 5-7 (halogen = Cl, Br, I) have been synthesized and their catalytic activity has been tested in HOCl/ClO- alkene epoxidations.These porphyrins are characterized by structural sepa
- Banfi, S.,Montanari, F.,Quici, S.
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p. 117 - 122
(2007/10/02)
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- Halogenation Using Quaternary Ammonium Polyhalides. XIV. Aromatic Bromination and Iodination of Arenes by Use of Benzyltrimethylammonium Polyhalides-Zinc Chloride System
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The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave brome- or iodo-substituted arenes in good yield, respectively.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Moriwaki, Masayuki,Tanaka, Toshio,Fujisaki, Shizuo,Okamoto, Tsuyoshi
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p. 439 - 443
(2007/10/02)
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- A SIMPLE METHOD FOR THE IODINATION OF AROMATIC COMPOUNDS
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The iodine - (trifluoroacetoxyiodo)benzene system is effective for the iodination of aromatic compounds, alkylbenzenes, various polynuclear aromatic hydrocarbons, halogenobenzenes, and some heterocyclic compounds.Trifluoroacetyl hypoiodite, which is a source of electrophilic iodine, is probably formed initially.Trifluoroacetyl hypoiodite can be generated in situ from (diacetoxyiodo)benzene and trifluoroacetic acid.
- Merkushev, E. B.,Yudina, N. D.
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p. 2320 - 2322
(2007/10/02)
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