6622-78-2Relevant academic research and scientific papers
Tetrabutylammonium dichlorobromide: An efficient and mild reagent for geminal bromochlorination of α-diazo carbonyl compounds
Shariff, Nusrathulla,Mathi, Selvam,Rameshkumar, Chidambaram,Emmanuvel, Lourdusamy
, p. 934 - 936 (2015)
An efficient and mild one-pot procedure for geminal bromochlorination of α-diazo carbonyl compounds has been developed for the first time using tetrabutylammonium dichlorobromide (TBADCB) via metal carbenoids. This protocol was found to be highly selectiv
TEMPO-Regulated Regio- and Stereoselective Cross-Dihalogenation with Dual Electrophilic X+ Reagents
Kong, Yi,Cao, Tongxiang,Zhu, Shifa
supporting information, p. 3004 - 3010 (2021/08/23)
A TEMPO catalyzed cross-dihalogenation reaction was established via redox-regulation of the otherwise complex system of dual electrophilic X+ reagents. Formally, the ICl, BrCl, I2 and Br2 were generated in-situ, which enabled high regio- or stereoselective access to a myriad of iodochlorination, bromochlorination and homo-dihalogenation products with a wide spectrum of functionalities. With its mild conditions and operational simplicity, this method could enable wide applications in organic synthesis, which was exemplified by divergent synthesis of two pharmaceuticals. Detailed mechanistic investigations via radical clock reaction, pinacol ring expansion and Hammett experiments were conducted, which confirmed the intermediacy of halonium ion. In addition, a dynamic catalytic model based on the versatile catalytic role of TEMPO was proposed to explain the selective outcomes.
Tetraalkylphosphonium trihalides. Room temperature ionic liquids as halogenation reagents
Cristiano, Rodrigo,Ma, Kefeng,Pottanat, George,Weiss, Richard G.
supporting information; experimental part, p. 9027 - 9033 (2010/03/30)
(Chemical Equation Presented) Six room temperature ionic liquids (RTILs) comprised of a tetraalkylphosphonium cation (tridecylmethyphosphonium or trihexyltetradecylphosphonium) and a trihalide anion (Br3 -, BrCl2-, or ClBr2-) have been prepared and characterized. Their ability to effect halogenation reactions with a variety of substrates has been explored. In general, halogenation reactions of alkenes proceed with high yields and stereo- and regioselectivities, whether performed in the absence or presence of a solvent (chloroform). Reactions of an alkyne and electrophilic substitution on an aromatic ring have been investigated as well. The facile preparation of the salts, their ease of handling, and the simplicity of product isolation should make these RTILs useful additions to the repertoire of halogenation reagents and the reagents of choice for specific transformations.
The generation and trapping of enantiopure bromonium ions
Braddock, D. Christopher,Hermitage, Stephen A.,Kwok, Lilian,Pouwer, Rebecca,Redmond, Joanna M.,White, Andrew J. P.
supporting information; experimental part, p. 1082 - 1084 (2009/07/10)
Enantiopure bromonium ions may be generated from enantiopure bromohydrins and derivatives, they can be trapped with an in situ nucleophile to give enantiomerically pure products. The Royal Society of Chemistry 2009.
A Simple and Convenient Method for Epoxidation of Olefins without Metal Catalysts
Klawonn, Markus,Bhor, Santosh,Mehltretter, Gerald,Doebler, Christian,Fischer, Christine,Beller, Matthias
, p. 389 - 392 (2007/10/03)
An easy method for epoxidation of olefins using bleach (sodium hypochlorite) and either a stoichiometric or catalytic amount of bromide ion has been developed. Without any transition metal catalyst a variety of non-activated olefins give epoxides in high yields and good selectivity at ambient conditions.
Stereoselective halogenations of alkenes and alkynes in ionic liquids
Chiappe, Cinzia,Capraro, Dario,Conte, Valeria,Pieraccini, Daniela
, p. 1061 - 1063 (2007/10/03)
(matrix presented) Room-temperature ionic liquids, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium bromide, and 1-butyl-3-methylimidazolium chloride, are used as "green" recyclabl
Bromochlorination of Alkenes with Dichlorobromate(1-) Ion. V. Regio- and Stereochemistry for the Bromochlorination of Styrene Derivatives with Dichlorobromate(1-) Ion in Protic Solvents
Negoro, Takeshi,Ikeda, Yoshitsugu
, p. 3519 - 3522 (2007/10/02)
The bromochlorination of styrene derivatives with tetrabutylammonium dichlorobromate(1-) (1) in such protic solvents as acetic acid and methanol gives the corresponding bromo chloro adducts along with substantial amounts of solvent-incorporated products i
REACTION OF t-BUTYL BROMIDE-DIMETHYL SULPHOXIDE: HALOGENATION AND MIXED HALOGENATION OF MULTIPLE BONDS
Dossena, Arnaldo,Marchelli, Rosangela,Casnati, Giuseppe
, p. 29 - 32 (2007/10/02)
The "t-butyl bromide-Me2SO" reagent brominates alkenes versus alkynes efficiently and selectively.By adding calcium chloride or potassium iodide to the system it is possible to obtain the corresponding dichloro or diiodo derivatives.By adding benzyltriethylammonium chloride to the system, bromochloro derivatives are obtained in good yields.The mechanism of the reactions is discussed.
BROMOCHLORINATION OF ALKENES WITH DICHLOROBROMATE(1 minus ) ION. I.
Negoro,Ikeda
, p. 2111 - 2115 (2007/10/02)
In the reaction of styrene with chlorine, the added bromide ions were mostly incorporated into the adduct, giving a bromo chloro compound. Tetrabutylammonium dichlorobromate(1 minus ) was found to be an efficient bromochlorinating agent. The reactions of 2-butenes and stilbenes were completely anti stereospecific.
