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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.
It is obtained by hydroboration of (−)‐α‐pinene with borane dimethyl sulfide. [7] Dialkylboranes are also rare for small alkyl groups. One common way of preparing them is the reduction of dialkylhalogenoboranes with metal hydrides. [8]
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]
It is used is for the production of borane dimethyl sulfide from diborane: [19] B 2 H 6 + 2 (CH 3) 2 S → 2 BH 3 ·S(CH 3) 2. Oxidation of dimethyl sulfide gives the solvent dimethyl sulfoxide. Further oxidation affords dimethyl sulfone. As illustrated above by the formation of its adduct with borane, dimethyl sulfide is a Lewis base.
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 ...
Boranes are chemical compounds of boron and hydrogen, with the generic formula of B x H y. These compounds do not occur in nature. Many of the boranes readily oxidise on contact with air, some violently. The parent member BH 3 is called borane, but it is known only in the gaseous state, and dimerises to form diborane, B 2 H 6. The larger ...
Borane(5) is the dihydrogen complex of borane. Its molecular formula is BH 5 or possibly BH 3 (η 2-H 2). [19] It is only stable at very low temperatures and its existence is confirmed in very low temperature. [20] [21] Borane(5) and methanium (CH 5 +) are isoelectronic. [22] Its conjugate base is the borohydride anion.
With respect to donor properties, dimethyl sulfide is a soft ligand with donor properties weaker than phosphine ligands. [3] Such complexes are generally prepared by treating the metal halide with the thioether. Chloro(dimethyl sulfide)gold(I) can however be prepared by redox reaction of elemental gold and DMSO in the presence of hydrochloric ...