L-selectride
Names | |
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IUPAC name
lithium tri-sec-butyl(hydrido)borate(1-)
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.049.166 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C12H28BLi | |
Molar mass | 190.10 g/mol |
Appearance | Colorless liquid |
Density | 0.870 g/ml |
Reacts with water | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Water reactive, flammable, burns skin and eyes |
Flash point | -17 °F |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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L-selectride is a
Use in synthesis
Like other borohydrides, reductions are effected in two steps: delivery of the hydride equivalent to give the lithium alkoxide followed by hydrolytic workup:
- R2CO + Li[(CH3CH2CH(CH3))3BH] → R2CHOLi + (CH3CH2CH(CH3))3B
- R2CHOLi + H2O → R2CHOH + LiOH
The selectivity of this reagent is illustrated by its reduction of all three methylcyclohexanones to the less stable methylcyclohexanols in >98% yield.[1]
Under certain conditions, L-selectride can selectively reduce
It reduces ketones to alcohols.[4] Aprepitant is another synthesis example where L-selectride was used.
Related compounds
N-selectride and K-selectride are related compounds, but instead of lithium as cation they have sodium and potassium cations respectively. These reagents can sometimes be used as alternatives to, for instance, sodium amalgam reductions in inorganic chemistry.[5]
References
- ^ ISBN 0-471-93623-5.
- ISBN 978-0-19-850346-0.
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