209259-55-2Relevant articles and documents
Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
Kinoshita, Hidenori,Kumaki, Wataru,Miura, Katsukiyo
, (2022/03/07)
Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.
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.
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.
