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Industrially, triethylborane is used as an initiator in radical reactions, where it is effective even at low temperatures. [1] As an initiator, it can replace some organotin compounds. It reacts with metal enolates , yielding enoxytriethylborates that can be alkylated at the α-carbon atom of the ketone more selectively than in its absence.
Compounds of the type BR n (OR) 3-n are called borinic esters (n = 2), boronic esters (n = 1), and borates (n = 0). Boronic acids are key to the Suzuki reaction. Trimethyl borate, debatably not an organoboron compound, is an intermediate in sodium borohydride production.
9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroboration reagent. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates. [1] 9-BBN is also known by its nickname 'banana borane'. [2]
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
The usual amount of the thickener is 6%. The amount of thickener can be decreased to 1% if other diluents are added. For example, n-hexane, can be used with increased safety by rendering the compound non-pyrophoric until the diluent evaporates, at which point a combined fireball results from both the triethylaluminium and the hexane vapors. [16]
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]
Diisopinocampheylborane is an organoborane that is useful for asymmetric synthesis. This colourless solid is the precursor to a range of related reagents. The compound was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes. The reagent is mainly used for the synthesis of chiral secondary ...
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 ...