- An efficient method for chlorination of alcohols using PPh3/Cl3CCONH2
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A new and convenient method for the chlorination of alcohols utilizing PPh3/Cl3CCONH2 is addressed. Various alcohols could smoothly be converted into their corresponding alkyl chlorides in high yield under mild conditions with short reaction times. A mechanism is disclosed with the evidence of inversion of configuration of the analogous alkyl chloride derived from R-(-)-2-octanol.
- Pluempanupat, Wanchai,Chavasiri, Warinthorn
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p. 6821 - 6823
(2007/10/03)
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- Rapid conversion of hindered arylsulfonates to alkyl chlorides with retention of configuration
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Arylsulfonates of hindered secondary alcohols are converted to the corresponding alkyl chlorides very rapidly and in good yields in the presence of titanium tetrachloride at low temperatures. These reactions proceed with exclusive retention of configuration.
- Lepore, Salvatore D.,Bhunia, Anjan K.,Mondal, Deboprosad,Cohn, Pamela C.,Lefkowitz, Craig
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p. 3285 - 3286
(2007/10/03)
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- Photocatalytic oxidation of alkanes with dioxygen by visible light and copper(II) and iron(III) chlorides: Preference oxidation of alkanes over alcohols and ketones
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Visible light irradiation of alkanes in acetonitrile with CuCl2 and FeCl3 catalysts under atmospheric dioxygen gave the corresponding alcohols and ketones effectively; in these reactions, the total selectivity of the products did not decrease so much with increase of alkane conversion. For example, cyclohexanol and cyclohexanone were formed with ca. 70% selectivity at 50% conversion, because overoxidation of the products took place more slowly than cyclohexane oxidation. The relative reactivity values of cycloalkanes increased as their ring-sizes decreased. In the oxidation of hexane, the reactivity ratio of C1-/C2-/C3-H was found to be 1.0/1.4/1.8 with CuCl2 and 1.0/4.6/6.6 with FeCl3, respectively. Toluene and diphenylmethane were more reactive than cyclohexane with FeCl3, as expected, whereas the alkane was oxidized faster than the benzylic compounds in the separate reaction with CuCl2. Moreover, the alkane oxidation could be comparably performed by sunlight instead of an artificial lamp.
- Takaki, Ken,Yamamoto, Jun,Komeyama, Kimihiro,Kawabata, Tomonori,Takehira, Katsuomi
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p. 2251 - 2255
(2007/10/03)
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- The functionalization of saturated hydrocarbons. Part 23. Gif-type bromination and chlorination of saturated hydrocarbons: A non-radical reaction
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The bromination of saturated hydrocarbons was studied in the GoAggIII system using CBrCl3 and other polyhaloalkanes. This bromination reaction was compared to free radical processes by (i) evaluating the rates of reactions for a series of polyhaloalkanes, by (ii) measuring the selectivity of the different systems towards various saturated hydrocarbons and by (iii) analyzing the product distribution arising from the bromination of cyclohexyl bromide under both the GoAggIII type conditions and from known processes for alkyl radical generation. Some chlorine containing reagents were also examined for C - Cl bond formation in the GoAggIII system. All the experimental findings support a mechanism for the reaction that is different from one involving free radicals. This non-radical pathway is common in all Gif-type systems, as seen in common patterns of selectivity, conditions is in agreement with a non-radical reaction pathway for the Gif-type bromination and chlorination reactions.
- Barton, Derek H. R.,Csuhai, Eva,Doller, Dario
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p. 9195 - 9206
(2007/10/02)
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