- Ytterbium triflate catalyzed synthesis of chlorinated lactones
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The direct synthesis of chlorolactones from differently substituted alkenoic acids, using either sodium hypochlorite or chloramine T as the source of electrophilic chlorine and ytterbium triflate hydrate as the Lewis acid is described. In both cases the r
- Genovese, Salvatore,Epifano, Francesco,Pelucchini, Caroline,Procopio, Antonio,Curini, Massimo
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- Indium chloride mediated chlorolactonization: Construction of chlorinated lactone fragments
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Chlorolactonization of unsaturated acids with chloramine-T catalyzed by indium chloride as a Lewis acid was demonstrated. This is a new synthetic methodology for the construction of chlorinated lactone frameworks from unsaturated acids.
- Abe, Hideki,Fukazawa, Naoki,Kobayashi, Toyoharu,Ito, Hisanaka
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- Dichlorination of olefins with diphenyl sulfoxide/oxalyl chloride
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The combination of diphenyl sulfoxide and oxalyl chloride was used to accomplish the dichlorination of olefins, in which chlorodiphenylsulfonium salt generated in situ was proposed to be the real active species as a chloronium ion source.
- Ding, Rui,Huang, Shuai,Wang, Qiyi,Liu, Yongguo,Sun, Baoguo,Tian, Hongyu
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supporting information
p. 2319 - 2330
(2020/07/03)
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- Chemoenzymatic Halocyclization of γ,δ-Unsaturated Carboxylic Acids and Alcohols
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A chemoenzymatic method for the halocyclization of unsaturated alcohols and acids by using the robust V-dependent chloroperoxidase from Curvularia inaequalis (CiVCPO) as catalyst has been developed for the in situ generation of hypohalites. A broad range of halolactones and cyclic haloethers are formed with excellent performance of the biocatalyst.
- Younes, Sabry H. H.,Tieves, Florian,Lan, Dongming,Wang, Yonghua,Süss, Philipp,Brundiek, Henrike,Wever, Ron,Hollmann, Frank
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- A Novel Method for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride
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A facile chlorolactonization of alkenoic acids by treatment with diphenyl sulfoxide/oxalyl chloride has been developed. The reaction can generate various chlorolactones in moderate to good yields, wherein the chlorodiphenylsufonium salt derived from diphenyl sulfoxide/oxalyl chloride serves as the source of Cl +.
- Ding, Rui,Lan, Liyuan,Li, Shuhui,Liu, Yongguo,Yang, Shaoxiang,Tian, Hongyu,Sun, Baoguo
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p. 2555 - 2566
(2018/05/03)
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- Dehydrogenative α-oxygenation of ethers with an iron catalyst
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Selective α-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective α-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.
- Gonzalez-De-Castro, Angela,Robertson, Craig M.,Xiao, Jianliang
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supporting information
p. 8350 - 8360
(2014/06/24)
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- Oxidative transformation of cyclic ethers/amines to lactones/lactams using a DIB/TBHP protocol
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A novel C-H oxidation of cyclic ethers and amines to the corresponding lactones and lactams was developed using a DIB/TBHP protocol. The reaction is mild and no metallic reagent is involved. In addition, study shows that the electronic properties of the substituents could affect the selectivity of oxidation. The Royal Society of Chemistry 2013.
- Zhao, Yi,Ang, Jascelyn Qian Lin,Ng, Angela Wan Ting,Yeung, Ying-Yeung
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p. 19765 - 19768
(2013/11/06)
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- An effective method for the preparation of chlorolactones
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The effective chlorolactonization of alkenoic acids with (diacetoxyiodo)benzene and lithium chloride under mild conditions have been studied. Experiments show that various 4-pentenoic acids react with (diacetoxyiodo)benzene and lithium chloride fluently in CH3OH at room temperature, obtaining five-membered chlorolactones in good yields in short times. Other alkenoic acids, such as 3-butenoic acid and trans 3-hexenoic acid give some more complicated results, and 4-pentynoic acid provides a chloroenol lactone with Z configuration in 40% of yield.
- Zhu, Min,Li, Li,Tong, Jiang Ying,Zhang, Hui
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experimental part
p. 431 - 434
(2012/01/03)
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- Synthesis of chlorinated β- and γ-lactones from unsaturated acids with sodium hypochlorite and Lewis acids
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The direct synthesis of several β- and γ-lactones used as electrophilic sources of chlorine, sodium hypochlorite and a Lewis acid is described. The scope and limitations of the method are discussed.
- López-López, José A.,Guerra, Francisco M.,Javier Moreno-Dorado,Jorge, Zacarías D.,Massanet, Guillermo M.
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p. 1749 - 1752
(2008/02/05)
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- METHYLENE-INDOLES, INDOLENINES AND INDOLENINIUM. XVII. REARRANGEMENT OF DE-ETHYLTABERSONINE IN ACETIC ACID
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De-ethyltabersonine 1 rearranged in boiling acetic acid to de-ethylcoronaridine 9 with a low yield.
- Wen, Ren,Laronze, Jean-Yves,Levy, Jean
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p. 1061 - 1065
(2007/10/02)
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- Process for manufacturing chlorolactones from unsaturated carboxylic acids
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Process for manufacturing chlorolactones by reacting, within an ahydrous organic solvent, a metal N-chlorosulfonamidate of the formula STR1 wherein R is a hydrogen or halogen atom or an alkyl radical, Ar is a mono- or polycyclic divalent aromatic radical and M is an alkali metal, with a substantially stoichiometrical proportion of an aliphatic or alicyclic carboxylic acid having at least one double bond separated from the COOH group by at least 2 carbon atoms, in the presence of a substantially stoichiometrical amount of a strong acid whose conjugate base is weakly nucleophilic.
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- 4-Pentenoic acid conversion
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A method for preparing a gamma-chloromethyl-gamma-butyrolactone which comprises contacting 4-pentenoic acid with air or oxygen and a catalyst comprising a noble metal halide, a variable valence transition metal halide and an alkali metal halide at a temperature between 50° and 200° C and superatmospheric pressure.
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