112595-55-8Relevant academic research and scientific papers
Chloro/bromotrimethylsilane-Cu(NO3)2·3H2O: Safe and efficient reagent system for the decarboxylative ipso-nitration and dibromination of cinnamic acids
Roshandel, Sahar,Gurung, Laxman,Mathew, Thomas,Prakash, G.K. Surya
supporting information, p. 2842 - 2845 (2017/06/27)
Further synthetic potential of halotrimethylsilane-nitrate salt mixture is revealed. A mixture of TMSX-Cu(NO3)2·3H2O system is found to be an efficient reagent system for both the decarboxylative nitration (ipso-nitration) when X?=?Cl, and dibromination of cinnamic acids, with X?=?Br, under mild conditions. The reactions are safe and simple, affording the corresponding products (E)-β-nitrostyrenes, and anti-2,3-dibromo-3-phenylpropanoic acids in high yields with high selectivity in a relatively short time. Use of hazardous and toxic nitrating systems such as acetyl nitrate and brominating agents such as molecular bromine can be avoided.
Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates
Chang, Dalu,Gu, Yang,Shen, Qilong
supporting information, p. 6074 - 6078 (2015/04/14)
Pd-catalyzed difluoromethylation of di-, tri- or tetra-substituted vinyl bromides, triflates, tosylates and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes. Vinyl fantasy: Pd-catalyzed difluoromethylation of di-, tri-, or tetra-substituted vinyl bromides, triflates, tosylates, and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes.
Convenient synthesis of terminal alkynes from anti-3-aryl-2,3- dibromopropanoic acids using a K2CO3/DMSO system
Cheng, Xuezhi,Jia, Jun,Kuang, Chunxiang
experimental part, p. 2350 - 2354 (2012/02/03)
A convenient, efficient, and generally applicable method was developed for the synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids in the presence of DMSO and K2CO3.
Gas-solid reactions of single crystals: A study of the reaction of bromine with single crystals of trans-cinnamic acid and a range of its derivatives by infrared and Raman microspectroscopy
Jenkins, Samantha L.,Almond, Matthew J.,Hollins, Peter
, p. 1966 - 1970 (2007/10/03)
Single crystals of trans-cinnamic acid and of a range of derivatives of this compound containing halogen substituents on the aromatic ring have been reacted with 165 Torr pressure of bromine vapour in a sealed desiccator at 20°C for 1 week. Infrared and Raman microspectroscopic examination of the crystals shows that bromination of the aliphatic double bond, but not of the aromatic ring, has occurred. It is demonstrated also that the reaction is truly gas-solid in nature. A time-dependent study of these reactions shows that they do not follow a smooth diffusion-controlled pathway. Rather the reactions appear to be inhomogeneous and to occur at defects within the crystal. The reaction products are seen to flake from the surface of the crystal. It is shown, therefore, that these are not single crystal to single crystal transitions, as have been observed previously for the photodimerisation of trans-cinnamic acid and several of its derivatives. It is shown that there are no by-products of the reaction and that finely ground samples react to form the same products as single crystals. The Owner Societies 2005.
Stereoselective synthesis of (E)-β-arylvinyl bromides by microwave-induced reaction of anti-3-aryl-2,3-dibromopropanoic acids using an AgOAc-AcOH system
Kuang, Chunxiang,Senboku, Hisanori,Tokuda, Masao
, p. 637 - 642 (2007/10/03)
(E)-β-Arylvinyl bromides were stereoselectively prepared in high yields by microwave irradiation of the corresponding anti-3-aryl-2,3- dibromopropanoic acids in AcOH in the presence of AgOAc for 0.5-3.0 min. (E)-β-Arylvinyl bromides were stereoselectively prepared in high yields by microwave irradiation of the corresponding anti-3-aryl-2,3-dibromo-propanoic acids in AcOH in the presence of AgOAc for 0.5-3.0 min.
Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction
Kuang, Chunxiang,Yang, Qing,Senboku, Hisanori,Tokuda, Masao
, p. 4043 - 4052 (2007/10/03)
(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time by microwave irradiation of the corresponding anti-2,3-dibromoalkanoic acids in a Et3N/DMF system. A one-pot synthesis of terminal alkynes and enynes from 2,3-dibromoalkanoic acids were also developed by microwave-induced reaction.
A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis β-bromostyrenes
Kim, Sun Hee,Wei, Han-Xun,Willis, Steven,Li, Guigen
, p. 4179 - 4185 (2007/10/03)
A new mild procedure has been developed for the synthesis of cis β- bromostyrene analogs with complete Z/E selectivity and good to excellent yields (58.4 - 90.9 %). The process involves carboxyl-halo-elimination of cinnamic acid dibromides by using triethylamine in N,N-dimethylformamide at room temperature. A one-pot procedure has also been described for the direct transformation of cinnamic acids to β-bromostyrenes.
Synthesis of the Substituted Z-1-Bromo-1-alkenes and Arylacetylenes from 2,3-Dibromocarboxylic Acids
Matveeva,Erin,Kurz
, p. 1065 - 1067 (2007/10/03)
Stereoselectivity was studied of simultaneous debromination-decarboxylation of dibrominated cinnamic and acrylic acids. The best selectivity in formation of Z-vinyl bromides was achieved with the use of organic nitrogen bases. The 1-bromo-1-alkenes were converted into the corresponding acetylenes.
