- Cu(OTf)2-catalyzed α-halogenation of ketones with 1,3-dichloro-5,5'-dimethylhydantoin and N-bromosuccinimide
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Copper(II) triflate catalyses efficiently the α-halogentaion of aryl or alkyl ketones with l.3-diehloro-5.5'-dimethylhydantoin and N-bromosuccinimde to give the corresponding α,α-dichloroketones and α-bromoketones in high yield with excellent product selectivity.
- Jagdale, Arun R.,Chouthaiwale, Pandurang V.,Sudalai, Arumugam
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experimental part
p. 1424 - 1430
(2010/02/28)
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- The α-Chlorination of Aryl Ketones with Manganese(III) Acetate in the presence of Chloride Ion
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The reaction of 2-(4-methoxyphenyl)-4-chromanone with Mn(OAc)3 in the presence of LiCl gave 3,3-dichloro-2-(4-methoxyphenyl)-4-chromanone.The reactions of 2-phenyl-4-chromanone, 1-phenyl-1-propanone, 1,2-diphenylethanone, and 1-tetralone similarly yielded α,α-dichloro derivatives in good yields. 2,2,2-Trichloroacetophenones were obtained from 2,2-dichloroacetophenones, but in the absence of LiCl, 2,2-dichloroacetophenones gave 2,2,3,3-tetrachloro-1,4-butanediones.KCl, NaCl, NH4Cl,AlCl3, and CaCl2 were also employed as the Cl- ion source.Synthetic applicability and the reaction mechanisms are discussed briefly.
- Tsuruta, Takehiko,Harada, Tetsuya,Nishino, Hiroshi,Kurosawa, Kazu
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p. 142 - 145
(2007/10/02)
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- Carbonyl Oxide Chemistry. The NIH Shift
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Benzophenone oxide has been shown to oxidize 1-chloronaphthalene and p-xylene with accompanying NIH shift of chlorine and methyl, respectively.Similar oxidation of toluene leads to a mixture of o-,p-, and m-cresols while N-acetyl-L-phenylalanine ethyl ester is oxidized to the corresponding tyrosine derivative.The results are discussed in terms of their relationship to the "activation" of polycyclic aromatic hydrocarbons in polluted atmospheres and the possible production of mutagens/carcinogens.
- Kumar, S.,Murray, R. W.
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p. 1040 - 1045
(2007/10/02)
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