87018-30-2Relevant academic research and scientific papers
Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-Anverene
Seidl, Frederick J.,Burns, Noah Z.
, p. 1361 - 1365 (2016)
The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the
A Highly Efficient Method for the Bromination of Alkenes, Alkynes and Ketones Using Dimethyl Sulfoxide and Oxalyl Bromide
Ding, Rui,Li, Jiaqi,Jiao, Wenyi,Han, Mengru,Liu, Yongguo,Tian, Hongyu,Sun, Baoguo
, p. 4325 - 4335 (2018/11/21)
The pairing of DMSO and oxalyl bromide is reported as a highly efficient brominating reagent for various alkenes, alkynes and ketones. This bromination approach demonstrates remarkable advantages, such as mild conditions, low cost, short reaction times, provides excellent yields in most cases and represents a very attractive alternative for the preparation of dibromides and α-bromoketones.
Bromination of alkenols with the H2O2 - LiBr - CeIII and H2O2 - LiBr - CeIV systems
Nikishin,Sokova,Kapustina
, p. 459 - 463 (2013/07/05)
Reactions of alkenols with H2O2 - LiBr - Ce(NO 3)3·6H2O or H2O2 - LiBr - Ce(NH4)2(NO3)6 system led to bromination of the double bond to yield vicinal dibromoalkanols. The reaction proceeded highly selectively, no oxidation of the hydroxyl group virtually occurred.
Regioselectivity of bromofluorination of functionalized 1-alkenes
Lübke, Martin,Skupin, Rolf,Haufe, Günter
, p. 125 - 133 (2007/10/03)
The regiochemistry of bromofluorinations of 1-alkenes with the combination of N-bromosuccinimide and amine/HF reagents mainly depends on the character of functional groups in the neighborhood of the double bond and only weakly from the fluorinating agent. While mono-substituted terminal alkenes mainly yield Markovnikov-oriented products, electron withdrawing groups in allylic or homoallylic position to the double bond destabilize carbenium centers in 2-position. Consequently, the part of anti-Markovnikov-oriented bromofluorides increases. Besides, with dropping reactivity of alkenes, the formation of dibromides becomes a competitive side reaction of bromofluorination. The extent of this process depends on the nature of the amine/HF reagent. This reaction is most important in case of the more nucleophilic trimethylamine bishydrofluoride, while this process is neglectible with pyridinium poly(hydrogen fluoride) (Olah's reagent).
