- The Effect of the Carbonyl Group, Phenyl Ring, and Ring Size of α-Iodo Cycloketones on the Nature of the Photochemical Carbon-Iodine Bond Cleavage
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UV irradiation of 2-iodo-3,4-dihydro-1(2H)-naphthalenone and 2-iodo-1-indanone has been found to involve competing radical and ionic photoprocesses.The carbonyl group, phenyl ring and ring size of cycloketones have an influence on the nature of the photochemical carbon-iodine bond cleavage.
- Sket, Boris,Zupan, Marko
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- α-iodination of ketones with MnO2/I2 reagent combination: A new environmentally friendly procedure
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In alcoholic media, α-iodination of ketones was accomplished using MnO2/I2 reagent combination in a new, environmentally friendly procedure. The reactions carried out under thermal conditions or microwave irradiation afforded α-iodo
- Le Bras, Gaelle,Provot, Olivier,Bekaert, Alain,Peyrat, Jean-Francois,Alami, Mouad,Brion, Jean-Daniel
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- IBX/I2-mediated oxidation of alkenes and alkynes in water: a facile synthesis of α-iodoketones
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The conversion of alkenes into α-iodoketones has been achieved in good yields and with high regioselectivity by means of iodohydrin formation and subsequent oxidation with 2-iodoxybenzoic acid (IBX) under mild conditions. Aromatic alkynes are also convert
- Yadav, Jhillu S.,Subba Reddy, Basi V.,Singh, Ashutosh P.,Basak, Ashok K.
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- One-pot reaction for the concise synthesis of spiro[benzofuran-2,2′-naphthalen]-1′-one derivatives
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A novel one-pot two-step protocol has been developed to synthesize various spiro[benzofuran-2,2′-naphthalen]-1′-one derivatives from the three-component reaction of tetralones, 2-hydroxyphenyl functionalized α,β-unsaturated ketones, and iodine. One C-C bond and one C-O bond have formed during this process. The notable features of this protocol are simple and mild reaction conditions, applicable to a wide range of readily available starting materials, good yields (up to 91%), and excellent stereoselectivities (up to 97:3).
- Hu, Jiaxing,Liu, Dandan,Xu, Wengang,Zhang, Fanglin,Zheng, Hua
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- Iodination of organic compounds with elemental iodine in the presence of hydrogen peroxide in ionic liquid media
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Iodo-transformations using the reagent system I2/H 2O2 were studied in the water miscible ionic liquid (IL) 1-butyl-3-methyl imidazolium tetrafluoroborate (bmimBF4) and in water immiscible IL, 1-butyl-3-methyl i
- Pavlinac, Jasminka,Laali, Kenneth K.,Zupan, Marko,Stavber, Stojan
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- Solvent-free iodination of organic molecules using the I 2/urea-H2O2 reagent system
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Introduction of iodine under solvent-free conditions into several aromatic compounds activated toward electrophilic functionalisation was found to proceed efficiently using elemental iodine in the presence of a solid oxidiser, the urea-H2O2 (UHP) adduct. Two types of iodo- functionalisation through an electrophilic process were observed: iodination of an aromatic ring, and side-chain iodo-functionalisation in the case of arylalkyl ketones. Two reaction routes were established based on the required substrate: iodine: oxidiser ratio for the most efficient iodo-transformation, and the role of UHP was elucidated in each route. The first, requiring a 1: 0.5: 0.6 stoichiometric ratio of substrate to iodine to UHP, followed the atom economy concept in regard to iodine and was valid in the case of aniline (1a), 4-t-Bu-phenol (3), 1,2-dimethoxy benzene (5a), 1,3-dimethoxy benzene (5b), 1,2,3-trimethoxy benzene (7a), 1,2,4-trimethoxy benzene (7b), 1,3,5-trimethoxy benzene (7c), 1-indanone (11a) and 1-tetralone (11b). The second reaction route, where a 1: 1: 1 stoichiometric ratio of substrate: I2: UHP was needed for efficient iodination, was suitable for side-chain iodo-functionalisations of acetophenone (1c) and methoxy-substituted acetophenones. Moreover, addition of iodine to 1-octene (13a) and some phenylacetylenic derivatives (15a, 15b) was found to proceed efficiently without the presence of any oxidiser and solvent at room temperature. This journal is The Royal Society of Chemistry.
- Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
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- IBX works efficiently under solvent free conditions in ball milling
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IBX (2-iodoxybenzoic acid), discovered in 1893, is an oxidant in synthetic chemistry whose extensive use is impeded by its explosiveness at high temperature and poor solubility in common organic solvents except DMSO. Since the discovery of Dess-Martin Periodinane in 1983, several modified IBX systems have been reported. However, under ball milling conditions, IBX works efficiently with various organic functionalities at ambient temperature under solvent free conditions. Also, the waste IBA (2-iodosobenzoic acid) produced from the reactions was in situ oxidized to IBX in the following step using oxone and thus reused for multiple cycles by conserving its efficiency (only ~6% loss after 15 cycles). This work describes an overview of a highly economical synthetic methodology which overcomes the problems of using IBX, efficiently in gram scale and in a non-explosive way. This journal is the Partner Organisations 2014.
- Achar, Tapas Kumar,Maiti, Saikat,Mal, Prasenjit
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p. 12834 - 12839
(2014/04/03)
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- M-iodosylbenzoic acid as a convenient recyclable hypervalent iodine oxidant for the synthesis of α-iodo ketones by oxidative iodination of ketones
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A convenient procedure for the preparation of -iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and -dicarbonyl compounds can be iodinated by thi
- Yusubov, Mehman S.,Yusubova, Rosa Y.,Funk, Tatyana V.,Chi, Ki-Whan,Kirschning, Andreas,Zhdankin, Viktor V.
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experimental part
p. 3681 - 3685
(2010/12/20)
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- An expedient protocol for conversion of olefins to α-bromo/iodoketones using IBX and NBS/NIS
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A variety of olefins have been shown to undergo conversion to the corresponding α-bromo/iodoketones when reacted with NBS/NIS and IBX in DMSO at room temperature. While the reaction is found to occur rapidly with e-rich arylolefins leading to the corresponding haloketones in 65-95% yields in 0.3-3.0 h, those containing e-withdrawing groups are found to yield diketones concomitantly, such that the latter are the exclusive products over extended duration of the reactions.
- Moorthy, Jarugu Narasimha,Senapati, Kalyan,Singhal, Nidhi
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experimental part
p. 2493 - 2496
(2009/08/17)
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- Highly efficient and clean method for direct α-iodination of aromatic ketones
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Under neutral reaction conditions, aromatic ketones were transformed into the corresponding α-iodo ketones in high yields by the combination of copper(II) oxide and iodine. The reaction mechanism showed that copper(II) oxide played multiple roles through random self-sorting. Georg Thieme Verlag Stuttgart.
- Yin, Guodong,Gao, Meng,She, Nengfang,Hu, Shengli,Wu, Anxin,Pan, Yuanjiang
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p. 3113 - 3116
(2008/09/16)
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- A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids
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Room temperature ionic liquids (ILs) are used as a green recyclable reaction media for the α-monohalogenation of 1,3-diketones, β-keto-esters and cyclic ketones with N-halosuccinimides in excellent yields in the absence of a catalyst. The recovered ionic liquid was reused five to six times with consistent activity.
- Meshram,Reddy,Vishnu,Sadashiv,Yadav
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p. 991 - 995
(2007/10/03)
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- Metal catalyst-free direct α-iodination of ketones with molecular iodine
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Ketones are directly converted to the corresponding α-iodoketones in good yields with molecular iodine under metal catalyst-free conditions. A significant difference in the reactivities was observed for aliphatic and aromatic ketones; whereas aliphatic ke
- Rao, Maddali L.N.,Jadhav, Deepak N.
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p. 6883 - 6886
(2007/10/03)
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- Efficient microwave induced direct α-halogenation of carbonyl compounds
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A novel and direct method for the synthesis of α-halocarbonyl compounds using sequential treatment of carbonyl compounds with [hydroxy(tosyloxy)iodo]benzene followed by magnesium halides under solvent-free microwave irradiation conditions is described.
- Lee, Jong Chan,Park, Jin Young,Yoon, So Young,Bae, Yong Hun,Lee, Seung Jun
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p. 191 - 193
(2007/10/03)
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- Efficient α-iodination of carbonyl compounds under solvent-free conditions using microwave irradiation
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Direct conversion of carbonyl compounds into α-iodocarbonyl compounds has been successfully achieved under solvent-free microwave irradiation conditions using N-iodosuccinimide and p-toluenesulfonic acid.
- Lee, Jong Chan,Bae, Yong Hun
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p. 507 - 508
(2007/10/03)
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- Iodination of enol acetates and 1,3-diones using N-iodosaccharin
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Iodination of enol acetates and 1,3-diones with N-iodosaccharin yielding the corresponding α-iodoketones and 2-iodo-1,3-diones is presented. Reactions are carried out at room temperature under neutral conditions and in short reaction times.
- Dolenc, Darko
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p. 2917 - 2924
(2007/10/03)
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- Direct α-iodination of ketones using iodine/SeO2
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A satisfactory yield one-pot synthesis of various α-mono iodoketones 2 was achieved by iodination under oxidative conditions of ketones 1. The monoiodination of different aliphatic or cyclic ketones (1-tetralones) showed the quite general applicability of
- Bekaert, Alain,Barberan, Olivier,Gervais, Marina,Brion, Jean-Daniel
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p. 2903 - 2905
(2007/10/03)
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- Efficient method for α-iodination of ketones
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α-Iodoketones are prepared in high yields from the initial reaction of various ketones with HNIB in CH3CN and subsequent treatment of potassium iodide or samarium(II) iodide.
- Lee, Jong Chan,Jin, Yong Suk
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p. 2769 - 2774
(2007/10/03)
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