2612-38-6Relevant articles and documents
Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide
Kumaki, Wataru,Kinoshita, Hidenori,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.
A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents
Spaggiari, Alberto,Vaccari, Daniele,Davoli, Paolo,Torre, Giovanni,Prati, Fabio
, p. 2216 - 2219 (2007/10/03)
A new application of (PhO)3P-halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.
Brominative Deoxygenation of Some Aldehydes and Ethers
Roman, Ulrich von,Knorr, Rudolf,Behringer, Claudia,Ruhdorfer, Jakob
, p. 260 - 262 (2007/10/02)
Three aldehydes (4a-c) are transformed into 1,1-dibromides (6a-c) by 2,2,2-tribromo-2,2-dihydro-1,3,2-benzodioxaphosphole (2).This reagent (2) is also very active in the cleavage of ethers; its reactions may show some features of carbonium as well as of SN2 character.