 | |
| Names | |
|---|---|
| IUPAC name lithium tri-sec-butyl(hydrido)borate(1-) | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider |
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| ECHA InfoCard | 100.049.166 |
| EC Number |
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| UNII | |
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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 | Water reactive, flammable, burns skin and eyes |
| Flash point | -17 °F |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
L-selectride is aorganoboron compound with thechemical formulaLi[(CH3CH2CH(CH3))3BH]. A colorless salt, it is usually dispensed as a solution in THF. As a particularly basic and bulkyborohydride, it is used for stereoselective reduction of ketones.[1]
Like other borohydrides, reductions are effected in two steps: delivery of the hydride equivalent to give the lithium alkoxide followed by hydrolytic workup:
The selectivity of this reagent is illustrated by its reduction of all threemethylcyclohexanones to the less stable methylcyclohexanols in >98% yield.
Under certain conditions, L-selectride can selectively reduceenones byconjugate addition of hydride, owing to the greater steric hindrance the bulky hydride reagent experiences at the carbonyl carbon relative to the (also-electrophilic) β-position.[2] L-Selectride can also stereoselectively reduce carbonyl groups in a 1,2-fashion, again due to the steric nature of the hydride reagent.[3]
It reduces ketones to alcohols.[4]
N-selectride andK-selectride are related compounds, but instead of lithium as cation they havesodium andpotassium cations respectively. These reagents can sometimes be used as alternatives to, for instance, sodium amalgam reductions in inorganic chemistry.[5]
