How do you quench borane dimethyl sulfide?
The excess borane is quenched by the slow addition of 125 mL of a 1:1 tetrahydrofuran–water solution followed by 750 mL of 5 M aqueous sodium hydroxide. The resulting two-phase mixture is heated at reflux for 12 hr, cooled to room temperature, and filtered through a coarse fritted funnel.
Is sme2 a reducing agent?
Furthermore, this method is also more efficient and selective for the deoxygenation of ketones to the corresponding alkenes, catalyzed by the same oxo-rhenium complex ReOCl3(SMe2)(OPPh3) employing PhSiH3 as a reducing agent, which produced a mixture of alkanes and alkenes in the reaction of several substrates, the …
Does borane reduce esters?
Borane also reduces aldehydes, ketones, lactones, epoxides, acids, tertiary amides, and nitriles but does not reduce esters.
What do you mean by Hydroboration?
In chemistry, hydroboration refers to the addition of a hydrogen-boron bond to C-C, C-N, and C-O double bonds, as well as C-C triple bonds. This chemical reaction is useful in the organic synthesis of organic compounds.
Does borane reduce ketones?
Borane is commonly used for the reduction of carboxylic acids in the presence of esters, lactones, amides, halides and other functional groups. In addition, borane rapidly reduces aldehydes, ketones, and alkenes. In addition, though highly flammable, gaseous diborane (B2H6) is available.
What is borane used for?
The main use of boranes is for the hydroboration of alkenes, one of the most versatile and useful reactions in organic synthesis. Borane also reduces aldehydes, ketones, lactones, epoxides, acids, tertiary amides, and nitriles but does not reduce esters.
What does borane reduce?
Why is hydroboration used?
What is hydroboration with example?
When 1,2-disubstituted alkenes are subjected to hydroboration, two organoboranes in a mixture is produced. Examples for these reactions can include the hydroboration-oxidation reaction of (E)-prop-1-en-1-ylbenzene. Another example would be the hydroboration-oxidation reaction of 1-methyl-cyclohex-1-ene.
What is borane write its characteristics and uses?
The main chemical application of boranes is the hydroboration reaction. Commercially available adducts such as borane–tetrahydrofuran or borane–dimethylsulfide are often used in this context as they have comparable effectiveness but without the hazard of handling highly reactive BH3 itself.
What is the meaning of hydroboration?
What is the purpose of borane dimethyl sulfide complex?
Borane dimethyl sulfide complex (BMS) is a commonly used reagent and a mediator for hydroboration reaction for the preparation of organoborane compounds, which are utilized as key intermediates in organic synthesis.
What is the CAS number for borane dimethyl sulfide?
Other names. BMS, Borane-dimethyl sulfide. Identifiers. CAS Number. 13292-87-0. 3D model ( JSmol) Interactive image.
What can be reduced by borane dimethylsulfide ( BMS )?
Reductions of aldehydes, ketones, epoxides, esters, and carboxylic acids give the corresponding alcohols. Lactones are reduced to diols, and nitriles are reduced to amines. Acid chlorides and nitro groups are not reduced by BMS. Borane dimethylsulfide is one of the most common bulk reducing agents used in the Corey–Itsuno reduction.
Which is better borane tetrahydrofuran or BMS?
The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility. BMS is commercially available at much higher concentrations than its tetrahydrofuran counterpart (10 M neat) and does not require sodium borohydride as a stabilizer, which could result in undesired side reactions.