67168-93-8Relevant academic research and scientific papers
A new selective dichlorination of C-C double bonds
Sakai, Kunikazu,Sugimoto, Kikuo,Shigeizumi, Sanae,Kondo, Kiyosi
, p. 737 - 740 (1994)
A new dichlorination procedure of C-C double bond was developed with hexachloroethane as chlorinating agent and RuCl2(PPh3)3 as catalyst. The reaction is highly selective for C-C double bond; other functional groups are un
Di-functionalization of alkenes using an oxidant generated from manganese(II) chloride under oxygen: Synthesis of γ-lactones
Hojo, Makoto,Murakami, Chikara,Ohno, Kaori,Kuboyama, Jun,Nakamura, Shin-Ya,Ito, Hajime,Hosomi, Akira
, p. 97 - 100 (1998)
Alkenes are oxidatively dichlorinated by stirring with manganese(II) chloride-lithium methoxide under oxygen atmosphere, followed by treatment with cone, hydrochloric acid. This di-functionalization of alkenes can be applied to the chlorolactonization of lithium 4-pentenoates.
Dichlorination of olefins with diphenyl sulfoxide/oxalyl chloride
Ding, Rui,Huang, Shuai,Wang, Qiyi,Liu, Yongguo,Sun, Baoguo,Tian, Hongyu
supporting information, p. 2319 - 2330 (2020/07/03)
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.
Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine
Cleveland, Alexander H.,Fronczek, Frank R.,Kartika, Rendy
, p. 3367 - 3377 (2018/03/26)
Herein we report a novel synthetic reaction to convert unactivated terminal aliphatic epoxide to alkyl vicinal dichloride based on triphosgene-pyridine activation. Our methodology is operationally simple and readily tolerated by a broad of scope of substrates as well as protecting groups. Furthermore, these mild conditions generally yield clean reaction mixtures that are free of byproducts upon aqueous workup.
Vanadium-catalyzed chlorination under molecular oxygen
Moriuchi, Toshiyuki,Fukui, Yasuhiro,Kato, Satoshi,Kajikawa, Tomomi,Hirao, Toshikazu
, p. 177 - 180 (2015/03/04)
A catalytic chlorination of ketones was performed by using a vanadium catalyst in the presence of Bu4NI and AlCl3 under atmospheric molecular oxygen. This catalytic chlorination could be applied to the chlorination of alkenes to give the corresponding vic-dichlorides. AlCl3 was found to serve as both a Lewis acid and a chloride source to induce the facile chlorination. A combination of Bu4NI and AlI3 in the presence of a vanadium catalyst under atmospheric molecular oxygen induced the iodination of ketones.
Rasta resin-triphenylphosphine oxides and their use as recyclable heterogeneous reagent precursors in halogenation reactions
Xia, Xuanshu,Toy, Patrick H.
, p. 1397 - 1405 (2014/07/22)
Heterogeneous polymer-supported triphenylphosphine oxides based on the rasta resin architecture have been synthesized, and applied as reagent precursors in a wide range of halogenation reactions. The rasta resin-triphenylphosphine oxides were reacted with either oxalyl chloride or oxalyl bromide to form the corresponding halophosphonium salts, and these in turn were reacted with alcohols, aldehydes, aziridines and epoxides to form halogenated products in high yields after simple purification. The polymersupported triphenylphosphine oxides formed as a byproduct during these reactions could be recovered and reused numerous times with no appreciable decrease in reactivity.
An effective dual copper-and sulfide-catalytic system for the epoxidation of aldehydes with phenyldiazomethane
Pereira, Ana,Martín, Carmen,Maya, Celia,Belderrain, Tomás R.,Pérez, Pedro J.
supporting information, p. 2942 - 2951 (2014/03/21)
Epoxides have been obtained from alde-hydes and phenyldiazomethane using catalytic amounts of both the copper homoscorpionate com-plexes Tp xCuL (Tpx = homoscorpionate ligand; L = acetonitrile or tetrahydrofuran, THF) and dimethyl sulfide (SMe2) in high yields and diasteroselectivities, and with activities higher (TOF = 46 h-1) than those already known with rhodium-or copper-based cata-lysts. Among the copper(I) homoscorpionate com-plexes tested, TpBr3Cu(NCCH 3) showed the highest catalytic activity under mild conditions. The catalytic activity is controlled by electronic effects induced by the Tp x ligand as well as by the stability of the TpxCu(SR 2) adducts. Indeed, in the case of TpMs as ligand, the TpMsCu(THT) (THT = tetrahydrothio-phene) and Tp MsCu(SMe2) species could be isolated as very stable crystalline solids, the molecular struc-ture of the former being confirmed by single-crystal X-ray diffraction analysis. The in situ generation of PhCHN 2 from benzaldehyde tosylhydrazone sodium salt at 60 °C in methyl tert-butyl ether as solvent and TpMsCu(THF) as the catalyst also showed high cata-lytic activities, improving those already reported with copper-based catalysts.
Catalysis of phosphorus(V)-mediated transformations: Dichlorination reactions of epoxides under appel conditions
Denton, Ross M.,Tang, Xiaoping,Przeslak, Adam
supporting information; experimental part, p. 4678 - 4681 (2010/12/24)
A stereospecific triphenylphosphine oxide-catalyzed 1,2-dichlorination reaction of epoxides has been developed. The reaction is effective for a range of terminal and internal epoxides. In contrast to the classical Appel-type dichlorination of epoxides, oxalyl chloride is used as a stoichiometric reagent to generate the chlorophosphonium salt responsible for dichlorination from catalytic triphenylphosphine oxide.
Reaction of Aromatic and Unsaturated Compounds with the Potassium Permanganate/HCI (HBr) Acetonitrile Reagent
Liu, Lilian Kao,Lin, Ching-Shan
, p. 61 - 66 (2007/10/03)
Addition of hydrochloric or hydrobromic acid to a solution of potassium permanganate in acetonitrile produced a homogeneous mixture, which is suitable for laboratory chlorination or bromination, respectively. Aromatic compounds more reactive than alkylbenzenes can be chlorinated or brominated without additional catalyst. Alkenes and alkynes give the corresponding vicinal dihaloalkanes and vinyl halides. All reactions complete within two hours under mild condition (25-60 °C) with excellent to moderate yields.
