87439-86-9Relevant academic research and scientific papers
Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones
An, Sejin,Moon, Da Yoon,Park, Bong Ser
, p. 6922 - 6928 (2018/10/24)
Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.
Silver-Catalyzed Decarboxylative Bromination of Aliphatic Carboxylic Acids
Tan, Xinqiang,Song, Tao,Wang, Zhentao,Chen, He,Cui, Lei,Li, Chaozhong
supporting information, p. 1634 - 1637 (2017/04/11)
The silver-catalyzed Hunsdiecker bromination of aliphatic carboxylic acids is described. With Ag(Phen)2OTf as the catalyst and dibromoisocyanuric acid as the brominating agent, various aliphatic carboxylic acids underwent decarboxylative bromination to provide the corresponding alkyl bromides under mild conditions. This method not only is efficient and general but also enjoys wide functional group compatibility. An oxidative radical mechanism involving Ag(II) intermediates is proposed.
Synthesis of β-haloketones by β-addition reactions of α,β-unsaturated ketones with BX3 (X = Br, Cl) as halide source
Lee, Adam Shih-Yuan,Wang, Shu-Huei,Chang, Yu-Ting
, p. 364 - 368 (2014/05/06)
A series of β-bromoketones and β-chloroketones were synthesized by the addition reactions of α,β-unsaturated ketones under BX 3 (X = Br, Cl) and ethylene glycol reaction system. The α,β-unsaturated ester also was successfully converted to its corresponding β-bromoester under the reaction condition. A series of β-bromoketones and β-chloroketones were synthesized by the addition reactions of α,β-unsaturated ketones under BX3 (X=Br, Cl) and ethylene glycol reaction system. Copyright
PHOTO-DEHALOGANATION OF VICINAL DIHALIDE TO OLEFIN
Izawa, Yasuji,Takeuchi, Masaki,Tomioka, Hideo
, p. 1297 - 1300 (2007/10/02)
Irradiation of vicinal dihalides in the presence of methanol or triethylamine resulted in an efficient dehalogenation to regenerate olefins.
