21428-65-9Relevant academic research and scientific papers
Efficient synthesis of some novel spiro heterocycles containing thiazole, oxazole, thiadiazole and triazolo-thiadiazole moiety under microwave irradiation
Dabholkar, Vijay V.,Mishra, Sushil Kumar J.
, p. 241 - 246 (2006)
5,5-Dimethyl cyclohexane-1,3-dione 1 was treated with twice the molar quantity of bromine in glacial acetic acid to yield 2,2-dibromo-5,5-dimethyl cyclohexane-1,3-dione 2. The dibromo compound 2 was subjected to reaction with substituted 2-aminothiophenol
Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates
Ito, Takatoshi,Iwai, Toshiyuki,Matsumoto, Fukashi,Sumino, Shuhei
, p. 8500 - 8507 (2021/06/28)
This work describes the synthesis of PCBM ([6,6]-phenyl-C61-butyric acid methyl ester) derivatives and other methanofullerene derivatives via generation of fullerene radical anions under photoirradiation and controlled by photoswitching, without preparation, a strong reducing agent, or precise control of the reaction conditions.
Production mechanism of active species on the oxidative bromination following perhydrolase activity
China, Hideyasu,Okada, Yutaka,Ogino, Hiroyasu
, p. 84 - 91 (2016/01/29)
Hypobromous acid and molecular bromine have been described as the active species involved in the oxidative bromination using perhydrolase, which catalyzes the reaction from acetic acid and hydrogen peroxide to peracetic acid (AcOOH). However, the brominating activity of them in a chemical model system was lower than that of the active species produced by the spontaneous reaction between AcOOH and Br-. Consequently, acetyl hypobromite (AcOBr) was suggested as new active species on the bromination by detection of the decarboxylation in the reaction between AcOOH and Br- and the strong brominating power with some tolerance against H2O2. Its production mechanism was explained as the ionic reaction involving the protonated intermediate of AcOOH by kinetic analysis.
Iridium-catalyzed isomerization/bromination of allylic alcohols: Synthesis of α-bromocarbonyl compounds
Gomez, Antonio Bermejo,Erbing, Elis,Batuecas, Maria,Vazquez-Romero, Ana,Martin-Matute, Belen
supporting information, p. 10703 - 10709 (2014/09/17)
α-Brominated ketones and aldehydes, with two adjacent electrophilic carbon atoms, are highly valuable synthetic intermediates in organic synthesis, however, their synthesis from unsymmetrical ketones is very challenging, and current methods suffer from low selectivity. We present a new, reliable, and efficient method for the synthesis of α-bromocarbonyl compounds in excellent yields and with excellent selectivities. Starting from allylic alcohols as the carbonyl precursors, the combination of a 1,3-hydrogen shift catalyzed by iridium(III) with an electrophilic bromination gives α-bromoketones and aldehydes in good to excellent yields. The selectivity of the process is determined by the structure of the starting allylic alcohol; thus, α-bromoketones formally derived from unsymmetrical ketones can be synthesized in a straightforward and selective manner. Synthon shuffle: An efficient and high-yielding synthetic route to prepare α-bromoketones and aldehydes is presented (see scheme, Cp=pentamethylcyclopentadienyl). The method relies on 1,3-hydrogen shift/bromination of allylic alcohols catalyzed by IrIII complexes. The products are obtained in excellent yields and as single constitutional isomers.
Solvent-free bromination reactions with sodium bromide and oxone promoted by mechanical milling
Wang, Guan-Wu,Gao, Jie
experimental part, p. 1125 - 1131 (2012/06/04)
New solvent-free brominations of 1,3-dicarbonyl compounds, phenols, various alkenes including chalcones, azachalcones, 4-phenylbut-3-en-2-one, methyl cinnamate, styrene and 1,3-cyclohexadiene were efficiently achieved by employing sodium bromide and oxone under mechanical milling conditions. The brominated products were obtained in good to excellent yields.
Design and application of 2,2-dibromodimedone as organic brominating reagent for asymmetric bromination of 1,3-dicarbonyl compounds and ketones catalysed by chiral amino acids
Goswami, Papori,Baruah, Abhilasha,Das, Babulal
experimental part, p. 1483 - 1487 (2011/02/23)
A green and ecofriendly enantioselective a-bromination of carbonyl and 1,3-dicarbonyl compounds is reported involving the synthesis of a novel organic brominating source. The organic brominating reagent can be recovered after each cycle, rebrominated and
A mild and environmentally acceptable synthetic protocol for chemoselective α-bromination of β-keto esters and 1,3-diketones
Khan, Abu T.,Goswami, Papori,Choudhury, Lokman H.
, p. 2751 - 2754 (2007/10/03)
A wide variety of unsubstituted β-keto esters can be brominated chemoselectively to the corresponding α-monobromo-β-keto esters by using a combination of vanadium pentoxide, hydrogen peroxide and ammonium bromide in a biphasic system, dichloromethane-wate
An efficacious method for the halogenation of β-dicarbonyl compounds under mildly acidic conditions
Meketa, Matthew L.,Mahajan, Yogesh R.,Weinreb, Steven M.
, p. 4749 - 4751 (2007/10/03)
A variety of 1,3-diketones, β-ketoesters and malonates can be chlorinated in high yields using sodium hypochlorite in a 5:2 mixture of acetone/acetic acid at 0°C for 1 h. Similarly, bromination of these dicarbonyl substrates can be accomplished under the same conditions using sodium hypobromite.
A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE and hydrohalic acid (HBr,HCl)
Kim, Kyoung-Mahn,Park, In-Hwan
, p. 2641 - 2644 (2007/10/03)
Mixtures of OXONE and hydrobromic acid or hydrochloric acid afford solutions of bromine or chlorine, respectively, α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared by addition of hydrobromic acid or hydrochloric acid to the mixture of
A new convenient bromination with KBrO3/KBr/Dowex
Kosmrlj, Janez,Kocevar, Marijan,Polanc, Slovenko
, p. 3583 - 3592 (2007/10/03)
Bromination of various 1,3-dicarbonyl compounds was achieved by using the mixture of potassium bromate and potassium bromide in the presence of Dowex 50X2-200 ion-exchange resin. Reactions were carried out under mild conditions and gave good yields of the
