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Hydroboration–oxidation reaction is a two-step hydration reaction that converts an alkene into an alcohol. [1] The process results in the syn addition of a hydrogen and a hydroxyl group where the double bond had been. Hydroboration–oxidation is an anti-Markovnikov reaction, with
This chemical reaction is useful in the organic synthesis of organic compounds. [1] Hydroboration produces organoborane compounds that react with a variety of reagents to produce useful compounds, such as alcohols, amines, or alkyl halides. The most widely known reaction of the organoboranes is oxidation to produce alcohols from alkenes.
Most reactions transfer a nucleophilic boron substituent to an electrophilic center either inter- or intramolecularly. In particular, α,β -unsaturated borates and borates with an α leaving group are highly susceptible to intramolecular 1,2-migration of a group from boron to the electrophilic α position.
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.
Disiamylborane (bis(1,2-dimethylpropyl)borane) is an organoborane with the formula [((CH 3) 2 CHCH(CH 3)) 2 BH] 2 (abbreviation: Sia 2 BH). It is a colorless waxy solid that is used in organic synthesis for hydroboration–oxidation reactions. Like most dialkyl boron hydrides, it has a dimeric structure with bridging hydrides.
In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne (−C≡CH) is added to a carbonyl group (C=O) to form an α-alkynyl alcohol (R 2 C(−OH)−C≡C−R). [1] [2] When the acetylide is formed from acetylene (HC≡CH), the reaction gives an α-ethynyl alcohol. This process is often referred to as ethynylation.
The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility. [1] BMS is commercially available at much higher concentrations than its tetrahydrofuran counterpart (10 M) and does not require sodium borohydride as a stabilizer, which could result in undesired side reactions. [2]
Thus, it is an intermediate in the preparation of diborane according to the reaction: [5] BX 3 +BH 4 − → HBX 3 − + (BH 3) (X=F, Cl, Br, I) 2 BH 3 → B 2 H 6. The standard enthalpy of dimerization of BH 3 is estimated to be −170 kJ mol −1. [6] The boron atom in BH 3 has 6 valence electrons.