- NaIO4-KI-NaN3 as a new reagent system for C-H functionalization in hydrocarbons
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The NaIO4-KI-NaN3 combination has been found to be an efficient, reliable, and inexpensive reagent system for mono- and 1,2-difunctionalization of hydrocarbons via C-H bond activation to afford vicinal azido- and acetoxy iodinations of cyclic hydrocarbons.
- Chouthaiwale, Pandurang V.,Suryavanshi, Gurunath,Sudalai, Arumugam
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scheme or table
p. 6401 - 6403
(2009/04/06)
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- Temperature dependence of pentyl nitrate formation from the reaction of pentyl peroxy radicals with NO
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Alkyl nitrate yields from the reaction of 1-pentyl, 2-pentyl and 2-methyl-2-butyl peroxy radicals with NO have been determined over the temperature range (261-305 K) and at 1 bar pressure from the photo-oxidation of the iodoalkane precursors in air-NO mixtures. Yields were observed to increase with decreasing temperature and, contrary to previous observations, along the series primary secondary ? tertiary. Our results suggests a significant temperature dependence for the formation of nitrates from the reaction of pentyl peroxy radicals with NO and represent an extension in the temperature range over which this reaction has been studied experimentally in the past. the Owner Societies.
- Cassanelli, Paola,Fox, David J.,Cox, R. Anthony
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p. 4332 - 4337
(2008/09/19)
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- Direct bromination and iodination of non-activated alkanes by hypohalite reagents
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The direct functionalisation of alkanes through bromination and iodination has been successfully achieved. The combination of stoichiometric mixtures of elemental halogen and sodium alkoxides leads to the formation of alkyl hypobromites and hypoiodites as reagents. The halogenation occurs without external photostimulation under thermal reaction conditions. Georg Thieme Verlag Stuttgart.
- Montoro, Raul,Wirth, Thomas
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p. 1473 - 1478
(2007/10/03)
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- New iodination reactions of saturated hydrocarbons
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Unactivated C-H bonds react with iodine when exposed to trimethylsilyl azide in the presence of a hypervalent iodine reagent or, alternatively, to aqueous H2O2, acetic anhydride, and sodium azide (see scheme). (Chemical Equation Presented).
- Barluenga, Jose,Campos-Gomez, Esther,Rodriguez, David,Gonzalez-Bobes, Francisco,Gonzalez, Jose M.
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p. 5851 - 5854
(2007/10/03)
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- Direct Iodination of Alkanes
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(Matrix presented) A cheap and efficient iodination of hydrocarbons can be achieved by generating tert-butyl hypoiodite from iodine and sodium tert-butoxide. The alkane is reactant and solvent, and this metal-free process provides a clean solution for their direct iodination.
- Montoro, Raul,Wirth, Thomas
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p. 4729 - 4731
(2007/10/03)
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- Photodecomposition of iodopentanes in air: Product distributions from the self-reactions of n-pentyl peroxyl radicals
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Product distributions from the 254-nm photooxidation of the three iodopentane isomers were explored as a technique for studying the self-reactions of individual pentyl peroxyl radicals (in air at ambient temperature and pressure). Pentanols and the associated carbonyl compounds (pentanal or pentanones) were major products as expected. Other major products resulted from the isomerization of pentan-1-oxyl and pentan-2-oxyl radicals, but their nature could not be identified. Minor products were alcohols and carbonyl compounds arising from the decomposition of pentoxyl radicals. Diols and mixed hydroxycarbonyl compounds from cross-combination reactions were essentially absent, in contrast to expectation. The observed product distributions were evaluated to derive branching ratios for the radical-preserving pathways of the self-reactions, 0.42 ± 0.17, 0.46 ± 0.10, 0.39 ± 0.08, for pentan-1-yl peroxyl, pentan-2-yl peroxyl, and pentan-3-yl peroxyl, respectively. Rate coefficients derived for the decomposition of the corresponding pentoxyl radicals, relative to their reaction with oxygen, are (5.1 ± 0.5) × 1018, (1.0 ± 0.2) × 1018, and (3.2 ± 0.3) × 1018 molecule cm-3, respectively. Rate constants for the isomerization of pentan-1-oxyl and pentan-2-oxyl were estimated from the contributions of isomerization products to the total amounts of products as (4.0 ± 1.1) × 105 s-1 and (1.0 ± 2.0) × 105 s-1, respectively.
- Heimann, Gerald,Benkelberg, Heinz-Jrgen,Bge, Olaf,Warneck, Peter
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p. 126 - 138
(2007/10/03)
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- First examples of superelectrophile initiated iodination of alkanes and cycloalkanes
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Direct iodination of alkanes and cycloalkanes in the presence of superelectrophiles has been accomplished for the first time. The reactions of saturated hydrocarbons with I2 in the presence of CCl4·2AlI3 at -20°C afforded monoiodides in good yields and selectivities.
- Akhrem, Irena,Orlinkov, Alexander,Vitt, Sergei,Chistyakov, Anatolii
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p. 1333 - 1335
(2007/10/03)
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- The first efficient iodination of unactivated aliphatic hydrocarbons
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No heavy metals, no enzymes, and a simple protocol: the direct iodination of aliphatic hydrocarbons, which has not been possible to date, can now be carried out in multiphase systems [see for example Eq. (l)]. In situ generated tetraiodomethane serves as a key intermediate in this selective radical chain reaction initiated by a single electron transfer. This room-temperature, efficient transformation is highly regioselective, easy to work-up, and hence widely applicable.
- Schreiner, Peter R.,Lauenstein, Oliver,Butova, Ekaterina D.,Fokin, Andrey A.
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p. 2786 - 2788
(2007/10/03)
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