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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 ...
9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example: [4] [5]. The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.
Solutions containing borane dimethylsulfide and borane–tetrahydrofuran are commercially available; in tetrahydrofuran a stabilising agent is added to prevent the THF from oxidising the borane. [8] A stability sequence for several common adducts of borane, estimated from spectroscopic and thermochemical data, is as follows:
A borane is a compound with the formula BR x H y although examples include multi-boron derivatives. A large family of boron hydride clusters is also known. In addition to some applications in organic chemistry , the boranes have attracted much attention as they exhibit structures and bonding that differs strongly from the patterns seen in ...
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] The adduct BH 3 (THF) is also commercially available as THF solutions. Its shelf life is less that BMS. [7] In terms of synthetic results, diborane or the more conveniently handle BMS and borane-THF are ...
For example, THF is converted, after hydrolysis, to 1-butanol. It also promotes certain variants of the Reformatskii reaction. [9] Triethylborane is the precursor to the reducing agents lithium triethylborohydride ("Superhydride") and sodium triethylborohydride. [10] MH + Et 3 B → MBHEt 3 (M = Li, Na)
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH 2) 4 O. The compound is classified as heterocyclic compound , specifically a cyclic ether . It is a colorless, water- miscible organic liquid with low viscosity .
The reaction was originally described by H.C. Brown in 1957 for the conversion of 1-hexene into 1-hexanol. [3] Hexanol synthesis. Knowing that the group containing the boron will be replaced by a hydroxyl group, it can be seen that the initial hydroboration step determines the regioselectivity. Hydroboration proceeds in an anti-Markovnikov manner.