Chemistry:Thexylborane
 Dimeric form of thexylborane
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3D model (JSmol)
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| C12H30B2 | |
| Molar mass | 195.99 g·mol−1 |
| Appearance | colorless liquid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Thexylborane is a borane with the formula [Me2CHCMe2BH2]2 (Me = methyl). The name derives from "t-hexylborane" (although the group is not the standard tert-hexyl group), and the formula is often abbreviated ThxBH2. A colorless liquid, it is a rare, easily accessed monoalkylborane. It is produced by the hydroboration of tetramethylethylene:[1]
- B2H6 + 2 Me2C=CMe2 → [Me2CHCMe2BH2]2
Reactions
Thexylborane is generated in situ. In solution, it isomerizes over the course several days to the 2,3-dimethyl-1-butyl derivative, shown as the monomer here:
- Me2CHCMe2BH2 → Me2CHCH(Me)CH2BH2
Thexylborane allows the synthesis of ketones by coupling a pair of alkenes with carbon monoxide, which serves as a carbonyl linchpin:[1]
- Me2CHCMe2BH2 + 2 RCH=CH2 → Me2CHCH(Me)CH2B(CH2CH2R)2
- Me2CHCH(Me)CH2B(CH2CH2R)2 + CO + H2O → O=C(CH2CH2R)2 + ...
An important feature of this reagent is that the thexyl group almost never undergoes anionotropic 1,2-migration from boron to a neighboring atom.[2]
References
- ↑ 1.0 1.1 Negishi, Ei-Ichi; Brown, Herbert C. (1974). "Thexylborane-A Highly Versatile Reagent for Organic Synthesis via Hydroboration". Synthesis 1974 (2): 77–89. doi:10.1055/s-1974-23248.
- ↑ Aggarwal, Varinder K.; Fang, Guang Yu; Ginesta, Xavier; Howells, Dean M.; Zaja, Mirko (2006-01-01). "Toward an understanding of the factors responsible for the 1,2-migration of alkyl groups in borate complexes" (in en). Pure and Applied Chemistry 78 (2): 215–229. doi:10.1351/pac200678020215. ISSN 1365-3075. https://www.degruyter.com/document/doi/10.1351/pac200678020215/html.
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