Oxidative bromination reactions in aqueous media by using Bu4NBr/TFA/H2O2 system was written by Moriuchi, Toshiyuki;Fukui, Yasuhiro;Sakuramoto, Takashi;Hirao, Toshikazu. And the article was included in Chemistry Letters in 2017.Category: ethers-buliding-blocks This article mentions the following:
Metal-free oxidative bromination reactions in aqueous media were performed using combination of tetrabutylammonium bromide as a a bromide source, trifluoroacetic acid as an acid and hydrogen peroxide as an oxidant under mild conditions. Oxidative bromination reaction of alkenes R1CH:CHR2 [R1 = HO(CH2)4, n-C8H17, PhCH2, R2 = H; R1 = Ph, R2 = HOCH2] and alkynes R3CCR4 (R3 = Ph, R4 = Me; R3 = R4 = MeOCH2) afforded the corresponding vicinal dibromides R1CHBrCHBrR2 and (E)-R3CBr:CR4Br, resp. Furthermore, this oxidative bromination system was applicable to the oxidative bromination of arenes, i.e. 2,6-dimethylphenol and 1,3,5-trimethoxybenzene, and 3,4-dihydronaphthalen-1(2H)-one. A gram-scale bromination reaction was also performed successfully. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Category: ethers-buliding-blocks).
1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Category: ethers-buliding-blocks
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem