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Borane dimethylsulfide (BMS) is a chemical compound with the chemical formula BH 3 ·S(CH 3) 2. It is an adduct between borane molecule ( BH 3 ) and dimethyl sulfide molecule ( S(CH 3 ) 2 ). It is a complexed borane reagent that is used for hydroborations and reductions .
Borane makes a strong adduct with triethylamine; using this adduct requires harsher conditions in hydroboration. This can be advantageous for cases such as hydroborating trienes to avoid polymerization. More sterically hindered tertiary and silyl amines can deliver borane to alkenes at room temperature. Borane(5) is the dihydrogen complex of
Borane dimethylsulfide (BMS) is a complexed borane reagent that is widely used for hydroborations. [4] Much of the original work on hydroboration employed diborane as a source of BH 3. Usually however, borane dimethylsulfide complex BH 3 S(CH 3) 2 (BMS) is used instead. [5] It can be obtained in highly concentrated forms. [6]
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH 3) 2 S. It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at 37 °C (99 °F).
Borane–tetrahydrofuran is an adduct derived from borane and tetrahydrofuran (THF). These solutions, which are colorless, are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds. A common alternative to BHF•THF is borane–dimethylsulfide, which has a longer shelf life and effects similar ...
In hydroboration, alkenes insert into borane B-H bonds, with anti-Markovnikov stereochemistry. Hydroboration occurs stereospecifically syn — on the same alkene face. The transition state for this concerted reaction can be visualized as a square with the corners occupied by carbon, carbon, hydrogen and boron, maximizing overlap between the ...
For example, borane-tetrahydrofuran, which often behaves equivalently to diborane, degrades to borate esters. Its adduct with dimethyl sulfide is an important reagent in organic synthesis. With ammonia diborane forms the diammoniate of diborane, DADB with small quantities of ammonia borane as byproduct. The ratio depends on the conditions.
Tris(2,2,2-trifluoroethyl) borate can be prepared by reaction of trifluoroethanol with boron trichloride, borane dimethylsulfide, boron tribromide, or boric anhydride. The latter is more convenient for larger scale preparations due to its low cost and ease of handling. [4] CF 3 CH 2 OH + B 2 O 3 → B(OCH 2 CF 3) 3. The product is purified by ...