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Potassium bis(trimethylsilyl)amide is used in the generation of K enolates. It is also used in the Wittig reaction, to give Li salt-free product distribution for selective (Z)-alkene formation and used with 18-crown-6 for selective formation of (Z)-?ß-unsaturated esters from phosphonates.
Kris F. Tesh.; Timothy P. Hanusa.; John C. Huffman. Ion pairing in [bis(trimethylsilyl)amido]potassium: The x-ray crystal structure of unsolvated [KN(SiMe3)2]2. Inorg. Chem. 1990, 29 (8), 1584-1586 .
Jörg Brüning. Lithium and potassium bis(trimethylsilyl)amide: Utilizing non-nucleophilic bases as nitrogen sources. Tetrahedron Letters. 1997, 38 (18), 3187-3188.
Sterically hindered strong base, compare Sodium bis(trimethylsilyl)amide, L13352 and Lithium bis(trimethylsilyl)amide, L15012. Used in the generation of K enolates, preferred to their Li or Na counterparts in some reactions, see e.g.: Tetrahedron Lett., 32, 1779 (1991); J. Am. Chem. Soc., 109, 6881 (1987); 111, 1063 (1989).
Also used in the Wittig reaction, to give Li salt-free product distribution for selective (Z)-alkene formation: J. Org. Chem., 45, 4260 (1980). Has also been used with 18-crown-6 for selective formation of (Z)-ɑß-unsaturated esters from phosphonates: Tetrahedron Lett., 24, 4405 (1983).
Hazard Statements: H225-H302-H333-H314-H318-H361-H336-H373-H304
Highly flammable liquid and vapour. Harmful if swallowed. May be harmful if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of damaging fertility or the unborn child. May cause drowsiness or dizziness. May cause damage to organs through prolonged or repeated exposure. May be fatal if swallowed and enters airways.
Precautionary Statements: P210-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.