1586-98-7Relevant academic research and scientific papers
Synthesis and extraction properties of oxathiacrown compounds containing benzyl groups
Rezekina,Rakhmanov,Lukovskaya,Bobylyova,Abramov,Chertkov,Khoroshutin,Anisimov
, p. 216 - 220 (2006)
8-Benzyl-1.4-dioxa-7,10-dithiacyclododecane and 11-benzyl-1,4,7-trioxa-10, 13-dithiacyclopentadecane were obtained by the interaction of (2,3-dibromo-1-propyl)benzene with 1,8-dimercapto-3,6-dioxaoctane and 1,11-dimercapto-3,6,9-trioxaundecane. The extrac
Dibrominated addition and substitution of alkenes catalyzed by Mn2(CO)10
Chan, Albert S. C.,Jiang, Yi,Meng, Shanshui,Song, Xianheng,Zhang, Hong,Zou, Yong
supporting information, p. 13385 - 13388 (2021/12/17)
A practical method for the dibromination of alkenes without using molecular bromine is consistently appealing in organic synthesis. Herein, we report Mn-catalyzed dibrominated addition and substitution of alkenes only with N-bromosuccinimide, producing a variety of synthetically valuable dibrominated compounds in moderate to high yields. This journal is
Electrochemical bromofunctionalization of alkenes in a flow reactor
Seitz, Jakob,Wirth, Thomas
supporting information, p. 6892 - 6896 (2021/08/20)
The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, thein situgeneration of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.
Closing the Gap: Structural Evidence for the Missing Hexabromide Dianion [Br6]2?
Sonnenberg, Karsten,Pr?hm, Patrick,Müller, Carsten,Beckers, Helmut,Steinhauer, Simon,Lentz, Dieter,Riedel, Sebastian
supporting information, p. 1072 - 1075 (2018/01/15)
The formation and experimental characterization of the first hexabromide dianion is presented. This dianion fills the last remaining gap in the series of polybromides from the tribromide [Br3]? to the undecabromide [Br11]
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.
Practical regio- and stereoselective azidation and amination of terminal alkenes
Ojo, Olatunji S.,Miranda, Octavio,Baumgardner, Kyle C.,Bugarin, Alejandro
supporting information, p. 9354 - 9358 (2019/01/03)
There is significant interest in developing more rapid and efficient production of nitrogen-containing allylic compounds, as widely used in various syntheses. This work reports a variety of allylic azides and allylic amines synthesized by an efficient, new one-pot protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)-isomer, under metal-free conditions. This process tolerates several functional groups including halogen-containing molecules; it is general for azides and amine nucleophiles; and, adducts were obtained in good yields.
Oxidative bromination reactions in aqueous media by using Bu4NBr/TFA/H2O2 system
Moriuchi, Toshiyuki,Fukui, Yasuhiro,Sakuramoto, Takashi,Hirao, Toshikazu
supporting information, p. 1708 - 1710 (2017/11/23)
Metal-free oxidative bromination reactions in aqueous media were performed using tetrabutylammonium bromide, trifluoroacetic acid, and hydrogen peroxide under mild conditions. Oxidative bromination reaction of alkenes was found to afford the corresponding vic-bromides. Furthermore, this oxidative bromination system is applicable to the oxidative bromination of alkynes, arenes, and 3,4-dihydronaphthalen-1(2H)-one. A gram-scale bromination reaction was also performed successfully.
Metal-free, regio- and stereoselective synthesis of linear (E)-allylic compounds using C, N, O, and S nucleophiles
Huang, Xiaojun,Fulton, Brandon,White, Kana,Bugarin, Alejandro
supporting information, p. 2594 - 2597 (2015/06/16)
A variety of allylic acetates and derivatives were synthesized by an efficient two-step protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)- isomer as the sole adduct. This process tolerates several functional groups including halogen-containing molecules, and it is general for weak oxygen, carbon, nitrogen, and sulfur nucleophiles. Furthermore, adducts were obtained in good to excellent yields.
Bromination of olefins with HBr and DMSO
Karki, Megha,Magolan, Jakob
, p. 3701 - 3707 (2015/04/22)
A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.
Brominations with Pr4NBr9 as a solid reagent with high reactivity and selectivity
Beck, Thorsten M.,Haller, Heike,Streuff, Jan,Riedel, Sebastian
, p. 740 - 747 (2014/04/03)
Tetrapropylammonium nonabromide (Pr4NBr9) is introduced as a room-temperature solid reagent for rapid bromination reactions of various substrates. The reagent exhibits reactivity similar to that of elemental bromine, but shows higher selectivity and it is easier and safer to store and to handle. Georg Thieme Verlag Stuttgart · New York.
