127154-65-8Relevant academic research and scientific papers
BROMOCHLORINATION OF ALKENES WITH DICHLOROBROMATE(1 minus ) ION. II. REGIO- AND STEREOCHEMISTRY FOR THE BROMOCHLORINATION OF 1-PHENYLPROPENES WITH DICHLOROBROMATE(1 minus ) ION.
Negoro,Ikeda
, p. 2116 - 2120 (1984)
The bromochlorinations of 1-phenylpropenes with tetrabutylammonium dichlorobromate(1 minus ) in aprotic solvents (dielectric constants 5-36) were found to be completely anti stereospecific and nonregiospecific, although Markownikoff adduct was mainly form
Concentration Dependence of the Steric Course of the Bromine Addition to Arylalkenes. The Case of Stilbenes
Belluci, Giuseppe,Bianchini, Roberto,Chiappe, Cinzia,Marioni, Franco
, p. 4094 - 4098 (1990)
The ratios of meso- to d,l-1,2-dibromo-1,2-diphenylethane obtained in the bromination of cis- and trans-stilbene in 1,2-dichloroethane have been determined by HPLC as a function of the reagent concentrations.With stoichiometric reagents both reactions wer
Green bromination method
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Paragraph 0065-0067, (2021/06/13)
The invention discloses a green bromination method, and belongs to the field of green organic chemistry. Under the conditions of room temperature, opening and neutrality, reaction raw materials are aromatic hydrocarbon, olefin, alkyne, tryptamine, tryptophane and derivatives thereof with different functional groups, a bromine source is MBrx (M is Fe , Fe , Ce and the like, and x is 2-3), and the unique oxidant is H2O2. Brominated alkanes, alkenes, aromatic hydrocarbons, pyrrolo-indolines and furo-indolines and derivatives thereof can be produced. The bromination reaction is carried out by using easily available and cheap reagents (such as FeBr2, CeB3 and H2O2) in the market and the solvent, and the method has the characteristics of mild reaction conditions, wide substrate application range, simple steps, easiness in operation and no need of separation, is a green, environment-friendly and safe bromination reaction method, and has a good application prospect.
A General Method for the Dibromination of Vicinal sp3C-H Bonds Exploiting Weak Solvent-Substrate Noncovalent Interactions
Qi, Zaojuan,Li, Weihe,Niu, Yanning,Benassi, Enrico,Qian, Bo
supporting information, p. 2399 - 2404 (2021/03/03)
A general procedure of 1,2-dibromination of vicinal sp3 C-H bonds of arylethanes using N-bromosuccinimide as the bromide reagent without an external initiator has been established. The modulation of the strength of the intermolecular noncovalent interactions between the solvent and arylethane ethanes, quantitatively evaluated via quantum chemical calculations, allows us to circumvent the fact that arylethane ethane cannot be dibrominated through traditional methods. The mechanism was explored by both experiments and quantum chemical calculations, revealing a radical chain with HAA process.
A Cascade Suzuki-Miyaura/Diels-Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin
Cain, David L.,McLaughlin, Calum,Molloy, John J.,Carpenter-Warren, Cameron,Anderson, Niall A.,Watson, Allan J. B.
supporting information, p. 787 - 791 (2019/04/25)
Cascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleo phile for cross-coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels-Alder regioselectivity was investigated and postsynthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.
Mild and Efficient Vicinal Dibromination of Olefins Mediated by Aqueous Ammonium Fluoride
Ng, Wing Hin,Shing, Tony K. M.,Yeung, Ying-Yeung
supporting information, p. 419 - 424 (2018/02/23)
A mild and efficient vicinal dibromination of olefins has been developed by using saturated aqueous ammonium fluoride solution as the promoter. Inexpensive and commercially available N -bromosuccinimide (NBS) was used as the brominating reagent. The corresponding vicinal dibromoalkanes could be obtained in good to excellent yields.
Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol
Takada, Yuki,Caner, Joaquim,Kaliyamoorthy, Selvam,Naka, Hiroshi,Saito, Susumu
supporting information, p. 18025 - 18032 (2017/12/08)
We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.
Efficient bromination of olefins, alkynes, and ketones with dimethyl sulfoxide and hydrobromic acid
Song, Song,Li, Xinwei,Sun, Xiang,Yuan, Yizhi,Jiao, Ning
supporting information, p. 3285 - 3289 (2015/06/25)
The oxidative bromination of olefins, alkynes, and ketones has been developed with HBr as the brominating reagent and DMSO as the mild oxidant. The simple conditions, high bromide-atom-economy, as well as easy accessibility and low cost of DMSO and HBr make the present strategy prospective for the synthesis of dibrominated alkanes, dibrominated alkenes and α-bromoketones.
Organocatalytic diastereoselective dibromination of alkenes
Zhu, Mingzhao,Lin, Shuangzheng,Zhao, Gui-Ling,Sun, Junliang,Córdova, Armando
experimental part, p. 2708 - 2712 (2010/07/04)
A highly diastereoselective pyrrolidine-promoted dibromination of alkenes by combination of NBS and succinimide is presented. The pyrrolidine-mediated dibromination of alkenes is higly anti-selective and gives the corresponding products in moderate to high yields and up to >25:1 dr.
The α-halogenation of α,β-unsaturated carbonyls and dihalogenation of alkenes using bisacetoxyiodobenzene/pyridine hydrohalides
Ngatimin, Marsewi,Gartshore, Christopher J.,Kindler, Jeremy P.,Naidu, Sudha,Lupton, David W.
scheme or table, p. 6008 - 6011 (2010/03/03)
A procedure for the α-chlorination or bromination of a number of α,β-unsaturated carbonyls, and the dichlorination or bromination of alkenes, is developed using bisacetoxyiodobenzene (BAIB) and the HCl or HBr salt of pyridine. The reaction proceeds in an
